Company PresentationDecember 15, 2020

1

Forward-Looking Statements

This presentation contains, and our other communications may contain, forward-looking statements within the meaning of Section 27A of the Securities Act of 1933, as amended, and Section21E of the Securities Exchange Act of 1934, as amended. These statements can be identified by the fact that they do not relate strictly to historical or current facts. Forward-looking statements,written, oral or otherwise made, represent the Company’s expectation or belief concerning future events. All forward-looking statements are subject to assumptions, risks, and uncertainties,which may change over time and many of which are beyond our control. The forward-looking statements contained in this presentation include statements related to the Company’s currentviews and expectations with respect to its future performance and operations and other anticipated future events and expectationsthat are not historical facts.

By nature, forward-looking statements involve risks and uncertainties that could cause actual results to differ materially from those projected or implied by the forward-looking statement.Forward-looking statements are based on current expectations and assumptions and currently available data and are neither predictions nor guarantees of future events or performance. Youshould not place undue reliance on forward-looking statements, which speak only as of the date hereof. Some of the factors that may cause actual results or other future events, circumstances,or aspirations to differ from those in forward-looking statements are described in the sections entitled “Risk Factors” and “Forward-Looking Statements” included in our Annual Report on Form10-K filed on June 9, 2020, or other applicable documents that are filed with the Securities and Exchange Commission (“SEC”). We do not undertake to update any forward- looking statement toreflect the impact of events, circumstances, or results that arise after the date that the statement was made. You, however, should consult further disclosures (including disclosures of a forward-looking nature) that we may make in any subsequent Annual Report on Form 10-K, Quarterly Report on Form 10-Q, Current Report on Form 8-K, or other applicable document that is filed withthe SEC, or in any document posted to the “Equity Investors” section of the Company’swebsite.

The unaudited estimates and statements included herein are the opinion of management and represent estimates and expectations based on the most current information available. While webelieve that our assumptions are reasonable, we caution that it is very difficult to predict the impact of known factors and it is impossible for us to anticipate all factors that could affect ouractual results. Our actual results may differ materially from these estimates. Our independent registered public accounting firm, BDO USA, LLP, has not audited, reviewed, compiled or performedany procedures with respect to any of the projections and forecasts contained in this presentation. Accordingly, BDO USA, LLP does not express an opinion or any other form of assurance withrespect thereto. As a result of the foregoing considerationsand limitations, investorsare cautioned not to place undue reliance on this projected financial information.

Non-GAAP Financial Measures

This presentation includes non-GAAP financial measures within the meaning of the federal securities laws, including Adjusted Operating Income, Adjusted EBITDA, and Adjusted EBITDA(Excluding Political). We define Adjusted Operating Income as operating income before the deduction of depreciation and amortization, stock-based compensation, corporate expenses,transaction costs, business realignment costs, impairment of goodwill, long-lived and intangible assets and net loss (gain) on sale and retirement of assets. We define Adjusted EBITDA as netincome (loss) before the deduction of income taxes, interest expense, net, repurchase of debt, transaction costs, depreciation and amortization, stock-based compensation, business realignmentcosts, impairment of goodwill, long-lived and intangible assets, impairment of investments, net (income) loss from discontinued operations, net of income taxes, net (loss) gain on sale andretirement of assets and other expense (income) net. We define Adjusted EBITDA (Excluding Political) as Adjusted EBITDA less political net revenue, net of a fifteen percent deduction to accountfor estimated national representative firm fees, music licensing fees and sales commissions expense. Adjusted Operating Income, Adjusted EBITDA, and Adjusted EBITDA (Excluding Political) donot represent, and should not be considered as alternatives to, net (loss) income or cash flows from operations as determined under U.S. generally accepted accounting principles, or GAAP. Areconciliation of these measures is included in the Appendix of this presentation orthe “Equity Investors” section of the Company’s website.

Disclaimer

This presentation is not directed to, or intended for distribution to or use by, any person or entity that is a citizen or resident located in any jurisdiction where such distribution, publication,availability or use would be contrary to law or regulation. The information contained in this presentation, including the forward-looking statements herein, is provided as of the date of thispresentation and may change materially in the future. Townsquare Media, Inc. (“Townsquare”) undertakes no obligation to update or keep current the information contained in thispresentation, whether as a result of new information, subsequent events or otherwise.

2

TABLE OF CONTENTS

Company and Industry Overview

Key Credit Highlights

Historical Financial Summary

3

Company and Industry Overview

4

(1) Financial results include certain pro forma adjustments to reflect current operations, and have been prepared consistent with past practices. Further Adjusted EBITDA is a non-GAAP financial measure. Please refer to the Appendix of this presentation for a reconciliation of Further Adjusted EBITDA to Net (loss) Income, the most directly comparable GAAP measure.

(2) Total broadcast audience represents the average of Townsquare’s Spring 2020 and Fall 2019 nationwide cume, P12+ M-Su 6a -6a, per Act 1 Systems (based on Nielsen data). Total digital audience represents average monthly global UVs on Townsquare’s owned and operated websites in the nine months ended September 30, 2020 per Google Analytics.

(3) Based on BIA Kelsey radio revenue estimates.

$375M / $71M

LTM 9/30/20 Revenue /

Further Adjusted EBITDA(1)

~$50M

Townsquare Ignite

2019 Revenue

44% / 44%

Q3’20 / YTD Sep. 2020

Revenue from Digital

Sources

11M / 58M

Total Broadcast / Digital

Audience(2)

#1 or #2

Position in 64 of 67

Markets(3)

INTRODUCTION TO TOWNSQUARE (NYSE: TSQ)

Key Stats

$68M / $20M

Townsquare Interactive

LTM 9/30/20 Net

Subscription Revenue /

Adjusted Operating Income

Townsquare is the leading local media, digital marketing, and live

events company focused on hundreds of underserved small and mid-sized

local markets across the U.S.

TSQ has invested in world-class technology and infrastructure to serve a broad

base of ~50,000 SMB clients and engage their loyal audiences

Presence outside the Top 50 markets is a competitive advantage given the

importance of local content in those markets as well as a weaker digital

competitive landscape

TSQ has successfully leveraged its radio platform to penetrate local markets

and build a full and comprehensive suite of digital marketing solutions

that meet its customers’ needs to grow their business

Solutions are greatly differentiated in TSQ’s markets vs. local digital agencies or

other competitors

44% of Townsquare’s net revenue is profitable digital revenue

TSQ has materially outperformed other peers in the broadcast/audio only

space during the pandemic, driven by digital revenue streams and local

market presence

Townsquare Interactive has delivered ~14% y/y growth throughout the pandemic

TSQ’s markets were not shut down or impacted to the same level as the Top 50

cities, and communities turned to our local brands in record setting numbers via

our digital platforms

5

DIGITAL

MARKETING

SOLUTIONS

DIGITAL PROGRAMMATIC

TECHNOLOGYPLATFORM

3,000+ active campaigns

/month(4)

Proprietary digital

programmatic platform

Organically built in 2014

Precision customer

targeting solutions

In-house Demand Supply

Platform (DSP) and media

buying & optimization

In-house Data Management

Platform (First Party Data)

In-house Creative Agency

BROADCAST

RADIO

Annual recurring heritageevents (e.g. WYRK’s Tasteof Country celebrated its20th anniversary in 2019)

Focused on providing family friendlyentertainment in our local markets

Monetizes the audience relationship and serves as strong branding and marketing for our own brands and for our clients

Note: UVs is defined as unique visitors. Branded Media and Digital Advertising Technology (Townsquare Ignite) make up the Advertising segment. Net Revenue and Adjusted Operating Income pro forma for the divestitures of our Arizona Bridal Shows business (consisting of two expositions) on March 18, 2019, as if it had occurred on January 1, 2019.1. Adjusted Operating Income is a non-GAAP financial measure. Please refer to page 2 for definitions of non-GAAP measures. Please refer to the Appendix of

this presentation for a reconciliation of LTM Adjusted Operating Income to Operating (loss) Income, the most directly comparable GAAP measure.

TOWNSQUARE SEGMENTS AT A GLANCE

$303M

$69M

Net Revenue

LTM Adjusted Operating Income(1)

interactive

$68M

$20M

LTM Net

Subscription

Revenue

LTM Adj

Operating Income(1)

$4M

$1M

LTM

Net Revenue

LTM Adjusted

Operating Income(1)

2. Represents the average of Townsquare’s Spring 2020 and Fall 2019 nationwide cume, P12+ M-Su 6a -6a, per Act 1 Systems (based on Nielsen data).

3. Represents average monthly global UVs on our owned and operated websites in the nine months ended September 30, 2020 per Google Analytics.

4. In Q3 2020.5. As of September 30, 2020.

Subscription-based revenue model

Organically built in 2012

Web and mobile sites

SEO, social media Management

Reputation monitoring and directory listings

Proprietary analytics and Insights

~600 employees in Charlotte, NC, including ~200 person Inside Sales Team selling across the entire U.S. focused on Small & Medium Sized Markets

LIVE EVENTS

6

11M Radio Listeners(2)

3rd Largest owner of radio

stations in the US

Geographic diversity in 67

U.S. markets outside Top 50

cities

Reach of 50% of the adult

population via AM/FM

broadcast in each market

Stable Listening Trends

(Time Spent Listening) and

Stable Audience given Local

DJs and Local Content

Strategy “Local First”

Live EventsTownsquare

InteractiveAdvertising

330+ Local websites

58M Total Website UVs(3)

322 Radio Stations

DIGITAL AMPED:

OWNED &

OPERATED

300+Local Station Apps

Includes XXL, Taste of

Country, Ultimate Classic

Rock, Loudwire, and

PopCrush

10 National leading

tastemaker music and

entertainment Brands

~21,900 SMB

customers(5)

More attractive competitive landscape

− Very limited focus from larger media players

− Starved for high quality local digital content given

the retrenchment of newspapers in these markets

− Very limited competition from digital marketing

solutions providers

− Very limited competition from digital programmatic

providers

Leading presence in 67 small and mid-sized

markets across the U.S.

– Portfolio of 322 radio stations with 330+ community

websites and 300+ local apps

– AM/FM broadcast alone reaches 50% of adults in

our markets

– #1 or #2 share of radio revenue in 64 markets

– Healthy, stable markets with lower economic

volatility and stabilizing institutions such as

universities, military installations and state capitals

– Average market population of ~300,000 people

Built world class Inside Sales Team (~180 people)

in Charlotte to focus on under-served digital

markets with population less than 1.5 million people

Original content and influential personalities drive

local engagement and compelling

marketing/advertising proposition for local

businesses

Major competitive advantage given retrenchment of

newspapers in these size markets

Google provided Townsquare a $260,000 grant to

build out news brands and operations in 2020

TOWNSQUARE LOCAL MARKET PRESENCE

Commentary Townsquare Markets

SELECT LOCAL RADIO AND DIGITAL MEDIA BRANDS

Chey enne

San Angelo

Augusta - WatervilleBismarck

Battle Creek

Wichita Falls

Twin Falls -Sun Valley

Texarkana

Grand Junction

Waterloo-Cedar Falls

Billings

Abilene

Rochester

Bangor

Lake Charles

Duluth-Superior

Tuscaloosa

Cedar Rapids

Danbury

Yakima

Manchester

BinghamtonSioux Falls

St. Cloud

Kalamazoo

New Bedf ord – Fall River

Richland – Kennewick - Pasco

Utica - Rome

Amarillo

Lubbock

Poughkeepsie

Odessa - Midland

Ev ansville – Owensboro

Rockford

Quad Cities Atlantic City - Cape May

Trenton

Ty ler –Longv iew

Flint

Killeen –Temple

Lansing

Presque Isle

Laf ayette

Fort Collins - Greeley

Portsmouth – Dover - RochesterOneontaBoise

El Paso

Albany - Schenectady - Troy

Buf f alo – Niagara Falls

Monmouth - Ocean

Shrev eport

Grand Rapids

Hudson Valley

Dubuque

Portland

7

TOWNSQUARE INTERACTIVE (TSI)(DIGITAL MARKETING SOLUTIONS)

Key Stats (1)

~30% profit margin (3)

~21,900 subscribers

~$300 average monthly subscriber fee

interactive

$79M annual run-rate net subscription revenue (2)

Note: Please refer to page 2 for definitions of non-GAAP measures.1. As of September 30, 2020.2. Based on subscribers as of September 30, 2020. 3. Represents Adjusted Operating Income margin for the trailing twelve months ended September 30, 2020.4. Multiple from FactSet as of 12/9/2020.5. LTM as of FY Q3 ended 9/30/2020.

TSI is a 100% owned, subscription-based business that provides website and digital marketing services to underserved SMBs

TSI enjoys a competitive advantage within our 67 small and mid-sized markets by leveraging our Local Sales Teams, trusted and long-standing local relationships and heritage brand recognition

A large dedicated Inside Sales Team of over 180 sellers also prospects small to mid-sized markets with demographics consistent with TSQ markets

TSI’s subscription revenue has grown on average approximately $10 million per year for 6 straight years, at a stable 30% margin since 2016

Net subscriber growth has been remarkably consistent, if not accelerating, even through a global pandemic

Approximately 57% of subscribers are outside of our local media market footprint

Large addressable market of nearly 9 million SMBs (500k within our markets)

Proprietary in-house technology and team

TSI employs ~600 dedicated professionals primarily based in Charlotte, NC

~14% YoY growth rate through pandemic

Proprietary software and support platform internally developed since 2012

Salesforce rolling out selling Ignite and other advertising products

~3,750 net subscribers added since 9/30/19, with ~2,900 YTD and ~1,150 added in Q3 alone

~21,900 net subscribers as of 9/30/20

~3,650 net subscribers added in 2019

10 consecutive quarters of >=850 net subscriber adds per quarter

Wix, a company which provides similar services to Townsquare Interactive, trades at a forward

revenue multiple of ~13x(4), despite having negative LTM

EBITDA(5)

8

TOWNSQUARE IGNITE(PROGRAMMATIC DIGITAL ADVERTISING)

Townsquare Ignite is an effective and efficient advertising solution that

enhances our local market presence, brands and trusted relationships

with sophisticated precision in-house audience targeting solutions

Hyper-targeted online audiences are delivered across desktop, mobile, apps, connected TV, email, paid search, and social media platforms utilizing display, video and native executions

Clients paying for highly effective ads, delivered to the right people at the right time Deliver far more precision and personalization of messaging and media, resulting in more efficiently targeted ad campaigns

Targeting Methods

Advanced Audience

Contextual

Re-targeting

Video

Social

Geolocation

Hyper-local Mobile

Foot Attribution

Search

Native

Programmatic Audio

White glove customer service with dedicated points of contact and rich campaign insights deliver strong results

Key Stats

In-house buying platform (DSP) integrated with 1,000+ exchanges accessing >250 billionimpressions/day

Majority of competitors use a single inventory source, making TSQ among the largest in-house trading desks

~3,300 Ignite campaigns live each month in Q3’20, ~2,800 LTM 9/30/20

Townsquare Ignite is our proprietary advertising technology platform that enables us to fulfill our client’s entire audience demand using:

TSQ digital inventory (on our owned and operated websites) andThird party advertising inventory across the Internet

9

~$50M in revenue in 2019

LIVE EVENTS

As a result of the COVID-19 pandemic, we have cancelled the majority of our live events in 2020, which has significantly impacted our Live Events revenue

Largely variable expense base helps offset the negative revenue impact

Live events are a natural extension of Townsquare’s core advertising offerings

Expands our audience and reinforces media brands through association

Strong local presence and marketing strength

Complementary advertiser offering without cannibalizing other revenue streams

Monetizes the listener/consumer relationship

Expertise in local markets and ability to syndicate events across Townsquare markets

TSQ creates, promotes and produces live events that are local, family oriented and community based in nature

Our events are largely perennial with strong customer loyalty

Low ongoing fixed cost, principally driven by innovation and human capital

Include concerts, expositions and other experiential events

In 2019, hosted ~200 live events and generated pro forma net revenue of $16.4M and $3.0M Adjusted Operating Income

~18% Adjusted Operating Income Margin

Select Local Live Event Brands

Note: Please refer to page 2 for definitions of non-GAAP measures. Pro forma for the divestiture our Arizona Bridal Shows business (consisting of two expositions) on March 18, 2019, as if it had occurred on January 1, 2019.

10

Key Credit Highlights

11

KEY CREDIT HIGHLIGHTS

1Attractive Free Cash Flow ProfileI

2Success in Digital Businesses Diversifying Revenue BaseII

3Attractive Radio Industry DynamicsIII

Leading Position in Small and Mid-sized MarketsIV

Leading Management TeamV

12

ATTRACTIVE FREE CASH FLOW PROFILE

Free Cash Flow Conversion (1)

Note: Please refer to page 2 for definitions of non-GAAP measures. 1. Free Cash Flow defined as Adjusted EBITDA less Capex, and Free Cash Flow Conversion defined as (Adjusted EBITDA – Capex) / Adjusted EBITDA. Free Cash Flow, Free Cash Flow Conversion, and Adjusted EBITDA are non-GAAP financial measures.

Please refer to page 2 for the definition of Adjusted EBITDA and the appendix of this presentation for a reconciliation of Adjusted EBITDA to Net (loss) Income, the most directly comparable GAAP measure.

$ FCF $74.2 $76.6 $82.7

Fast growing, profitable digital revenue is complemented by stable broadcast revenue with attractive margins (digital 44% of total net revenue YTD 9/30/20).

Increasing contribution from subscription-based Townsquare Interactive segment (TSI)

– ~$79mm Q3 run-rate revenue; ~30% of total net revenue YTD 9/30/20

– Stable 30% margin

Diverse revenue segments and operating scale reduce earnings volatility

Low, predictable capex requirements (<5% of revenue)

Substantial tax shields related to the tax amortization of intangible assets

I

$43.6

82% 81% 81%73%

2017 2018 2019 LTM 9/30/2020

13

44%

11%

Townsquare(YTD 9/30/20)

Radio Broadcasters(Industry Average)

$32

$40

$49

$62 $68

2016 2017 2018 2019 LTM9/30/20

Note: Please refer to page 2 for definitions of non-GAAP measures.1. Represents Adjusted Operating Income Margin for trailing twelve months ended September 30, 2020.2. Represents year-over-year revenue growth trends.3. Per reported YTD 2020 digital revenue for iHeart, Cumulus, Beasley, Salem, and Saga as of September 30, 2020.

Townsquare’s Digital Evolution

Key Stats

Revenue ($M) and Growth Trends(2)

Townsquare Interactive

YTD 9/30/202018 Revenue

Percentage of Ad Revenue from Digital Sales

+7.5% revenue growth in YTD 2020 as of 9/30/2020

3000+ Ignite campaigns live each month in Q3’20

In-house buying platform (DSP) integrated with 1,000+ exchanges accessing >250 billion impressions/day

~$50M in revenue in 2019

Total Addressable Market: 8.9M U.S. SMBs and >$32B

~ 21,900 subscribers as of 9/30/20

30% profit margin(1)

~ $300 average monthly subscriber fee

Approximately 57% of TSQ subscribers are outside of TSQ’s local media market footprint

(3)

Townsquare Interactive and Townsquare Ignite have delivered positive revenue growth during the first nine months of 2020 despite the COVID-19 pandemic, with TSI delivering positive revenue growth throughout every month of the year, demonstrating TSQ’s perceived value to its clients

+53% +14%+27% +21% +27%

Townsquare Ignite

Key Stats

SUCCESS IN IGNITE AND INTERACTIVE BUSINESSES IS DRIVING THE COMPANY’S DIGITAL TRANSFORMATION

II

Digital businesses supports long-term growth and diversification away from radio advertising

Digital28%

Digital44%

14

$66

$43

$15 $9

Primetime TV 30sSpot

Newspaper Radio 30s Spot Outdoor

RADIO: A STABLE FOUNDATION WITH AN ATTRACTIVE VALUE PROPOSITION

1. Nielsen Audio RADAR reports (131, 135, 139, 143), Mon-Sun, 12M-12M.2. Edison Research, “Share of Ear,” 2019, P13+.3. Nielsen Total Audience Report Q1 2019.4. Based on 2018-2019 metrics for Adults ages 25 to 54.

Radio Reaches Everyone Radio’s Audience is Growing

Radio Delivers Results at an Attractive PriceRadio Delivers a Local Connection

Radio megaphone with proven ability to activate audience to action

Large, local salesforce with direct relationships with local advertisers

Compelling live and local content on heritage brands

First party audience data collection and insights

Ability to produce curated local content absent from national and social media platforms

Radio is still one of the most cost-effective and efficient ways for local advertisers to reach the masses and local communities

Unlike certain other traditional media, radio’s audience is growing

The introduction of streaming, mobile apps and smart speakers have helped to increase radio’s total audience

Radio usage has remained substantially unchanged since 1970, reaching ~90% of Americans 12+ (1)

Radio dominates listening hours, with 45% vs. Streaming Audio’s 15%, YouTube’s 11% and SiriusXM’s 7% share of listening (2)

Radio reaches more people per week than any other media

Radio

PC

TV

Smartphone

Tablet

229M

224M

199M

113M

132M

Weekly Reach (P18+) (3)

Radio’s Weekly Reach (P12+) (1)

2016 2017 2018 2019

247.7M 247.4M 274.9M 248.4M

New attribution tools, such as Analytic Owl, are providing ways to measure broadcast campaigns that have historically not existed

Average CPM by Ad Medium(4)

III

15

Townsquare operates in 67 small and mid-sized markets

across the US, with virtually no presence in the top 50

markets

More attractive competitive landscape

– Limited focus from larger media players

– Starved for high quality media and entertainment experiences

– Limited competition from advertising technology and digital marketing solutions providers

Healthy, stable markets with lower economic volatility and stabilizing institutions such as universities, military installations and state capitals

TSQ reaches a majority of the population in its markets

TSQ has trusted relationships between its heritage brands and its audience and strong local relationships with its advertisers

TSQ’s ability to bring national products, technology and practices to small and mid-sized markets is unique

– Our national scale and expertise allows us to develop market leading products and services, and provide training and support to our local markets

Opportunity in Small and Mid-Sized Markets(1)

On average, markets in which TSQ operates have seen a lower level of unemployment versus the national average

Unemployment Rate(2)

(Count of Townsquare Markets by DMA Rank)

No Presence

Average Townsquare market population: ~300k (50k – 1mm)

1. Source: Nielsen, Fall 2019.2. Bureau of Labor Statistics; TSQ averages based on simple average of local market footprint.

IV SMALL AND MID-SIZED MARKET STRATEGY IS A COMPETITIVE ADVANTAGE

78

17

14

5

16

0 - 50 51 - 99 100 - 149 150 - 199 200 - 249 250+ Unranked

4.8% 4.6%4.2%

3.8% 3.6%

7.9%

5.3%4.9%

4.4%3.9% 3.7%

8.5%

2015 2016 2017 2018 2019 Aug-20

TSQ Average National Average

Inside Sales Team in Charlotte focused on serving cities with under 1.5 Million people

16

EXPERIENCED MANAGEMENT TEAM

President of AOL Media SVP, Worldwide Marketing at

Bertelsmann Music Group 10+ years at Townsquare

Bill WilsonChief Executive Officer

(In current role since 2017)

Owner and Managing Principal of AMG Financial

EVP and CFO of LiveWire Ventures EVP and CFO of PriCellular

Corporation (sold in 1998 for$1.4bn)

10+ years at Townsquare

Stu RosensteinEVP, Chief Financial Officer(In current role since 2010)

Associate at Bear Stearns and BrownBrothers Harriman

Analyst at JP Morgan

10+ years at Townsquare

Scott SchatzEVP, Finance & Operations(In current role since 2015)

President of GAP West Leadership roles at Bonneville

Communications, Clear Channel andKatz Radio

10+ years at Townsquare

Erik HellumEVP, COO Local Media

(In current role since 2017)

Vice President, Design and Product atAOL Media

10+ years at Townsquare

Managing Director at MESA Securities

Director at Credit Suisse 7+ years at Townsquare

Associate at Oak Hill Capital Partners Analyst at Merrill Lynch

9+ years at Townsquare

Vice President, Human Resources atWorld Wrestling Entertainment(WWE)

6+ years at Townsquare

Alyssa GoldbergSVP, Human Resources

(In current role since 2014)

Claire YenicayEVP, Investor Relations

(In current role since 2015)

Sun SachsSVP, Product & Engineering(In current role since 2010)

Michael JosephsEVP, Bus. Dev. & M&A

(In current role since 2015)

V

17

Historical Financial Summary

18

$74 $77 $83

$44

2017 2018 2019 LTM 9/30/20

$16 $18 $20

$16

2017 2018 2019 LTM 9/30/20

$318 $339 $353 $303

$40 $49

$62

$68 $32

$20 $17

$4

$390 $408

$431

$375

2017 2018 2019 LTM 9/30/20

Advertising Townsquare Interactive Live Events

Net Revenue Adjusted EBITDA (% Margin) (1)

Capital Expenditures (% of Total Revenue) Unlevered Free Cash Flow (% Conversion)(2)

($ in millions)

1. Adjusted EBITDA is a non-GAAP financial measure. Please refer to page 2 for the definition of Adjusted EBITDA and the appendix of this presentation for a reconciliation of Adjusted EBITDA to Net (loss) Income, the most directly comparable GAAP measure. 2017 – 2019 metrics exclusive of cost savings.

2. Unlevered Free Cash Flow is defined as Adjusted EBITDA less Capital Expenditures. % Conversion is defined as Adjusted EBITDA less Capital Expenditures divided by Adjusted EBITDA. LTM 9/30/20 unlevered Free Cash flow excludes cost savings of $11mm.

HISTORICAL FINANCIAL PERFORMANCE

4% 4% 5% 4% 82% 81% 81% 73%

23% 23% 24% 16%

19

$90 $95 $102

$60

$11

$71

2017 2018 2019 LTM 9/30/20

Adj. EBITDA Cost Savings

Net Revenue Commentary

($ in millions)

Note: Adjusted EBITDA is a non-GAAP financial measure. Please refer to page 2 for the definition of Adjusted EBITDA. Please refer to the applicable quarterly earnings release included in the “Equity Investors” section of the Company’s website for a reconciliation of Adjusted EBITDA to Net (loss) Income, the most directly comparable GAAP measure. Financial results include certain pro forma adjustments to reflect current operations, and have been prepared consistent with past practices.

2020 CONTINUES TO IMPROVE

Adjusted EBITDA

TSI Revenue

Although TSQ have been impacted by the

COVID-19 pandemic, the Company has

seen continued sequential improvement

since April 2020

– Prior to the onset of the pandemic, TSQ had a

strong start to 2020, with YTD February 2020

PF revenue and PF Adjusted EBITDA

increasing 6% and 16%, respectively

– TSQ’s small market presence has greatly

benefited the Company, as TSQ’s markets

opened sooner than many of the big cities

– In addition, the strength of TSQ’s digital

products and services, which have been more

resilient than broadcast advertising, have

helped to offset overall revenue declines

In total, Digital revenue increased by 7% in Q3

− Townsquare Ignite and AMPED (advertising on

TSQ’s owned and operated local websites)

revenue declines were less severe than TSQ’s

other advertising offerings, and each returned

to positive revenue growth in July

− TSI has proven to be recession resistant,

growing revenue and subscribers each month

throughout the pandemic

TSQ has prudently managed cash and generated

positive Cash Flow from Operations though the first

9 months of 2020

– Cash declined by $6mm YTD, driven by

principal debt repayment ($15M) and dividends

($4M)

Q2: -35%

$21.8 $24.6 $27.6 $29.8 $31.9 $33.8

Apr May Jun Jul Aug Sep

Q3: -15%

$5.5 $5.6 $5.8 $5.9 $6.1 $6.2

Apr May Jun Jul Aug Sep

Q2: +10% Q3: +14%

$15.5

$2.1

$17.5

Q1 Q2 Q3

20

1. Also excludes advertising related to the 2018 World Cup.2. Represents same station results (excludes acquisitions/divestitures). Salem and Saga’s ex political numbers are not available on a same station basis. 3. Not pro forma for podcasting acquisitions.4. Not pro forma for Jelli and Stuff Media acquisitions, acquired in Q4 2018.5. Pro forma for acquisitions.

WE HAVE OUTPERFORMED THE MARKET IN 2019 AND 2020 YTD

(9.0%)

(1.9%)

0.3% 1.4%

3.0% 4.2%

6.7%

(3) (2) (1) (5)

TSQ continues to lead its radio competitors in performance and outlook, driven by our streamlined

“Local First” story, with stability in core business and digital growth drivers

Net Revenue Excluding Political

Net Revenue Including Political

(3) (2) (2) (5)

(13.9%)

(4.8%) (4.3%)

(1.1%) (1.0%)

0.1% 1.9% 2.0%

4.8%

(2) (4)

(4)

(Radio)(Radio)

(Radio) (Radio)

2019 Net Revenue Growth

21

Ex Political: NA NA (30.7%) (35.4%) NA NA NA (26.6%) (19.2%) NA

YTD EBITDA:(6) $21 $46 $43 $7 $4 ($0) $4 $273 $35 $26

YoY Delta ($23) ($183) ($120) ($32) ($41) $1 ($16) ($421) ($42) ($7)

(34.3%)

(31.1%)(29.5%) (28.5%) (27.3%) (26.9%) (26.5%)

(24.3%)

(17.5%)

(6.6%)

1 2 3 4 5 6 7 8 9 10

YTD September 2020 Net Revenue Growth

Note: Dollars in millions. Please refer to page 2 for definitions of non-GAAP measures.1. GAAP results. Does not adjust for the divestiture of WDMK-FM in Detroit to Beasley on August 31, 2019.2. GAAP results. The impact of the station swap with Cumulus effective 3/1/19 (ETM got NASH FM in NYC and 2 stations in Springfield, MA in exchange for 3 Indianapolis stations); the divestiture of WAAF-FM in Boston to EMF (effective 2/22/20); and the

acquisitions of podcast companies Cadence13 and Pineapple Media are not defined.3. Represents same station results (excludes acquisitions/divestitures). 4. GAAP results. Does not adjust for the acquisition of WDMK-FM in Detroit from Urban One on August 31, 2019.5. Net revenue pro forma for the divestiture of Bridal in Q1 2019. Adjusted EBITDA is a non-GAAP financial measure. Please refer to page 2 for a definition of Adjusted EBITDA. Please refer to the applicable quarterly earnings release included in the “Equity

Investors” section of the Company’s website for a reconciliation of Adjusted EBITDA to Net (loss) Income, the most directly comparable GAAP measure.6. For companies showing radio segment results, represents radio segment BCF/SOI/OIBDA (Urban One, Univision, Entravision and Salem). Beasley’s EBITDA is not available, so providing SOI. Otherwise represents total company EBITDA.

(2) (1) (3) (4) (1)

Salem results driven by their foundation of stable

Christian block programming, which

represents ~25% of revenue and was down <2% in Q2

and Q3

(5)

Across the industry, radio operators were hit especially hard by the COVID-19 pandemic, however, largely due

to cost cuts were able to generate positive EBITDA in Q3. TSQ continues to lead its radio competitors in

performance driven by our digital strategy, advertising and marketing solutions

WE HAVE OUTPERFORMED THE MARKET IN 2019 AND 2020 YTD

(Radio) (Radio) (Radio) (Radio)

22

Ex Political: (31.4%) (34.5%) (31.1%) (35.3%) (29.1%) NA (30.1%) (25.1%) (18.8%) (6.1%)

Q3 EBITDA:(4) $31 $12 $20 $10 $8 $6 $2 $162 $18 $11

YoY Delta ($67) ($5) ($40) ($8) ($9) ($3) $1 ($113) ($11) ($0)

(30.5%) (29.7%) (29.4%)

(26.7%)(24.9%)

(22.8%) (22.0%) (21.5%)

(15.3%)

(2.4%)

1 2 3 4 5 6 7 8 9 10

Q3 Net Revenue Growth

Note: Dollars in millions. Please refer to page 2 for definitions of non-GAAP measures.1. GAAP results. The impact of the divestiture of WAAF-FM in Boston to EMF (effective 2/22/20); and the acquisitions of podcast companies Cadence13 and Pineapple Street Media in Q3’19 are not defined. 2. Represents same station results (excludes acquisitions/divestitures). 3. GAAP results. Does not adjust for the acquisition of WDMK-FM in Detroit on August 31, 2019.4. For companies showing radio segment results, represents radio segment BCF/SOI/OIBDA (Urban One, Univision, Entravision and Salem). Beasley and Saga’s EBITDA is not available so SOI is provided. Otherwise represents total company EBITDA.5. Adjusted EBITDA is a non-GAAP financial measure. Please refer to page 2 for a definition of Adjusted EBITDA. Please refer to the applicable quarterly earnings release included in the “Equity Investors” section of the Company’s website for a reconciliation

of Adjusted EBITDA to Net (loss) Income, the most directly comparable GAAP measure.

(1) (2) (2) (3) (2)

Salem results driven by their foundation of stable

Christian block programming, which

represents ~25% of revenue and was down <2% in Q3

WE HAVE OUTPERFORMED THE MARKET IN 2019 AND 2020 YTD

(Radio) (Radio) (Radio) (Radio)

23

(5)

TOWNSQUARE’S DIGITAL PLATFORM DRIVES GROWTH

24

As of LTM 9/30/20, TSQ’s digital revenue grew +10% y/y ($158M)

Our digital revenue strength helped offset declines in broadcast

advertising revenue and live events revenue as a result of the

pandemic, driving industry leading performance

TSQ’s digital platform is truly a differentiator among radio

broadcasters, where most operators have a much smaller digital

offering (although many have started to heavily invest in

podcasting)

Note: TSQ pro forma for acquisitions and divestitures.1. Q3’20 data for all operators.

Digital % of Net Revenue(1)

TSQ’s Digital Revenue Growth ($M)

10% 10%

15% 18%

44%

% of Total 22% 25% 29% 35% 42%

$88

$99

$120

$153 $158

2016 2017 2018 2019 LTM9/30/20

Y/Y

Growth:+12% +22% +27% +10%

Appendix

25

THIRD QUARTER 2020 HIGHLIGHTS

Q3 2020 improved significantly over Q2 2020 trough levels as business improved each month throughout the quarter

Q3 2020 net revenue declined -15.3% to $95.4 million, showing sequential improvement throughout the quarter (July -20.7%, August -16.3% and September -8.8%)

Q3 2020 Adjusted EBITDA(1) declined -37.8% to $17.5 million (up from Q2 2020’s $2.1 million)

Total digital revenue exceeded 44% of total net revenue in Q3 2020 and YTD September 2020

Townsquare Interactive continued to outperform, as net subscription revenue and subscriber counts continue to grow each month

Q3 2020 TSI net subscription revenue and Adjusted Operating Income(2) increased +14.5% and +9.8%, respectively

TSI’s subscriber base grew by ~1,150 subscribers (to ~21,900), the 10th consecutive quarter of at least 850 net subscribers adds (and the most quarterly net adds in nearly 6 years)

Although Townsquare’s Advertising net revenue was severely impacted due to the pandemic, Q3 rebounded

Q3 2020 Advertising net revenue declined -17.2% (from Q2 2020’s -37.5%), strengthening throughout the quarter (July -23.3%, August -18.0% and September -10.2%)

1. Adjusted EBITDA is a non-GAAP financial measure. Please refer to page 2 for a definition of Adjusted EBITDA. Please refer to the applicab le quarterly earnings release included in the “Equity Investors” section of the Company’s website for a reconciliation of Adjusted EBITDA to Net (loss) Income, the most directly comparable GAAP measure.

2. Adjusted Operating Income is a non-GAAP financial measure. Please refer to page 2 for a definition of Adjusted Operating Income. Please refer to the applicable quarterly earnings released included in the “Equity Investors” section of the Company’s websit e for a reconciliation of Adjusted Operating Income to Operating (loss) Income, the most directly comparable GAAP measure.

26

THIRD QUARTER 2020 HIGHLIGHTS (CONT’D)

Townsquare took a number of actions in order to solidify its liquidity position

Enacted a series of cost reduction efforts to help mitigate revenue declines due to the COVID-19 pandemic, including fixed operating expense savings related to a reduction in workforce, the temporary elimination of 401K matching program and various other measures, in addition to variable expense declines such as sales commissions

In total, Q3 2020 direct operating expenses declined $6.1 million, or -8% vs prior year and YTD 2020 direct operating expenses declined $14.6 million, or -7%

Eliminated discretionary capital expenditures beginning in Q2 2020, targeting an estimated 15% capex reduction in 2020 vs. prior year (savings of ~$3M)

Q3 2020 capex declined $2.7 million, or -48%, vs prior year; YTD 2020 capex declined $3.3 million, or -23% vs. prior year (already surpassing FY 2020 savings goal)

Deferred the payment of certain payroll taxes under The CARES Act until 2021 and 2022

The Company’s board of directors elected to cease paying quarterly dividends (~$8 million of annualized savings, and ~$4 million in 2020) (1)

Generated $12.0 million of Cash Flow from Continuing Operations in Q3 2020, and $23.8 million YTD September 2020

Used only $5.6 million of cash in YTD 2020, in addition to reducing debt by $14.7 million and paying $4.2 million of dividends

Generated $9.1 million of cash in Q3 2020

1. The Company’s final dividend payment was paid on May 15, 2020 to shareholders of record as of April 2, 2020.27

ADJUSTED EBITDA RECONCILIATION

Note: Adjusted EBITDA is a non-GAAP financial measure. Please refer to page 2 for a definition of this measure. 28

LTM

($ in millions) # 2017 2018 2019 9/30/2020

Net (loss) income ($12.9) ($97.3) ($65.7) ($163.4)

Provision (benefit) from income taxes (7.5) 30.8 (14.6) (55.3)

Interest expense, net 32.8 34.3 33.9 31.9

Gain on repurchase of debt -- (0.1) -- (1.2)

Depreciation and amortization 18.4 19.6 25.8 21.0

Stock-based compensation 0.7 1.6 2.6 2.1

Transaction costs 1.2 1.5 1.5 3.7

Business realignment costs 1.3 1.4 0.2 2.6

Impairment of goodwill and intangible assets [1] 20.6 48.2 108.7 217.5

Other [2] 35.4 54.7 9.9 0.9

Adjusted EBITDA $90.0 $94.7 $102.4 $60.0

Business manager reorganization [3] 0.5

Headcount reductions [4] 6.4

Nielsen cost savings [5] 4.6

Further Adjusted EBITDA $71.5

1. In 2019 and 1H’20, TSQ took significant non-cash impairment charges to the value of its FCC licenses, primarily due to a change in valuation methodology adopted after discussion with its new auditors. Beginning with the 2019 audit, TSQ no longer utilizes the revenue and cash flows from Townsquare Ignite, Townsquare Interactive and Live Events to support the intangible assets and goodwill that is associated with the radio stations, which is significantly different than how the Company valued TSQ’s intangible assets and goodwill since the inception of TSQ in 2010. As a reminder, impairment charges are purely non-cash charges and do not impact TSQ’s net revenue, direct operating expenses, Adjusted EBITDA or cash balance.

2. Includes impairment loss on investment, net loss from discontinued operations, net loss (gain) on sale and retirement of assets and other (income) expense

3. In October 2020, Townsquare enacted a reorganization whereby its Business Managers are now placed on functional teams focused on specific business tasks across all markets (i.e. ledger recording, forecasting/budgeting, fixed assets, cash applications, etc.) versus prior focus on local market coverage across all business tasks. Resulted in the elimination of 8 Business Managers and ~$500k in cost savings per annum

4. Adjustment reflects the elimination of 185 full time positions primarily across 12 departments, including in connection with COVID-19, resulting in annualized cost savings of ~$13 million. The Company does not intend to replace these positions going forward, unless sales levels justify additional hires

5. Reflects the annualized sales expense savings related to the Company’s decision to eliminate its Nielsen contract in certain smaller markets. Townsquare has notified Nielsen of its intention to modify its contract. Note, the Company will maintain its Nielsen contract in certain of its larger markets

Commentary

ADJUSTED OPERATING INCOME RECONCILIATION

Note: Please refer to page 2 for definitions of non-GAAP measures.

Advertising

Townsquare

Interactive

Live

Events

LTM LTM LTM

($ in millions) 9/30/2020 9/30/2020 9/30/2020

Operating (loss) income ($160.0) $19.3 ($0.9)

Depreciation and amortization 11.6 0.5 0.5

Stock-based compensation 0.2 0.1 0.0

Business realignment costs (0.2) -- 0.3

Impairment of goodwill 68.8 -- --

Impairment of intangible and long-lived assets 148.1 -- 0.6

Adjusted Operating Income $68.6 $20.0 $0.5

29

30