Forward-Looking Statements and Non-GAAP Financial Measures

Forward-Looking Statements and Non-GAAP Financial Measures 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 Section 21E 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. 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. You should 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 Form 10-K filed on March 13, 2018, or other applicable documents that are filed or furnished with the Securities and Exchange Commission ( SEC ). We do not undertake to update any forward- looking statement to reflect 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 or furnished with the SEC, or in any document posted to the Equity Investors section of the Company s website. 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 we believe 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 our actual results. Our actual results may differ materially from these estimates due to the completion of our financial closing procedures, final adjustments and other developments that may arise between now and the time the financial results for our fourth quarter are finalized. This preliminary financial data has been prepared by and is the responsibility of management. Our independent registered public accounting firm, RSM US LLP, has not audited, reviewed, compiled or performed any procedures with respect to the accompanying preliminary financial data. Accordingly, RSM US LLP does not express an opinion or any other form of assurance with respect thereto. As a result of the foregoing considerations and limitations, investors are cautioned not to place undue reliance on this projected financial information. This presentation includes non-gaap financial measures within the meaning of the federal securities laws, including Adjusted EBITDA, Adjusted EBITDA Less Interest, Capex and Taxes and Adjusted Segment Operating Income. We define Adjusted EBITDA as net income (loss) before the deduction of income taxes, other (income) expense, net, interest expense, net, repurchase of debt, transaction costs, stock based compensation, net (gain) loss on sale and retirement of assets, business realignment costs, goodwill and other intangible impairment charges, net (loss) income from discontinued operations, net of income taxes, impairment on investment and depreciation and amortization. Adjusted EBITDA Less Interest, Capex and Taxes is defined as Adjusted EBITDA less net cash interest expense, capital expenditures and cash paid for taxes. Adjusted Segment Operating Income is defined as segment operating income before the deduction of depreciation and amortization, stock-based compensation, business realignment costs and goodwill and other intangible impairment charges. Adjusted EBITDA, Adjusted EBITDA Less Interest, Capex and Taxes and Adjusted Segment Operating Income do not represent, and should not be considered as alternatives to, net (loss) income, cash flows from operations or segment operating income (loss), as determined under U.S. generally accepted accounting principles, or GAAP. For a reconciliation of these measures to net income or segment operating income, see Exhibit 99.1 to our Current Reports on Form 8-K filed with the SEC on March 13, 2018. Townsquare 2

Introduction to Townsquare Radio, digital media, entertainment and digital marketing solutions company that focuses primarily on small to mid-sized markets Owns and operates market-leading radio, live event, and digital, mobile, video and social media properties National scale with a hyper-local focus Live & local content Diversified multi-channel growth strategy Townsquare 3

Townsquare by the Numbers We reach millions of engaged consumers Local Marketing Solutions 325+ local websites 317 radio stations 300+ local station apps Local Media 12+ million listeners (1) ~13 million UVs (2) Digital Marketing Solutions (Townsquare Interactive) ~12,400 customers (3) Entertainment ~350 live events per year Live Events ~18 million annual attendees 391 YouTube Channels 21+ Million Social Media Followers (4) 9 O&O national websites 20+ million UVs (2) National Media Note: UVs is defined as unique visitors. O&O is defined as owned and operated. (1) Represents the average of Townsquare s Spring 2017 and Fall 2017 nationwide cume, P12+ M-Su 12a -12a, per Act 1 Systems (based on Nielsen data). (2) Represents average monthly global UVs in 2017 per Google Analytics. (3) As of December 31, 2017. (4) Includes Facebook fans, Twitter followers and YouTube subscribers on our owned and operated properties as of December 31, 2017. Townsquare 4

Townsquare Reaches Middle America Key Takeaways So many marketing programs are oriented toward metro elite imagery Marketing needs to reflect less of New York and Los Angeles culture and more of Des Moines and Scranton. More and more, advertisers have been narrowing their focus to big markets, which often reside on the coasts, and largely ignore middle America Townsquare reaches millions of Americans across its radio, digital and live event properties in small and midsized markets Townsquare is an and buy, not an or buy, complementing big market advertising buys with little to no over audience overlap Townsquare 5

The Small & Mid-Sized Market Opportunity Townsquare s Local Marketing Solutions offerings target small and mid-sized markets across the U.S. Community focused populations Strong local relationships between media providers and advertisers Attractive competitive landscape Under-served in high quality media and entertainment experiences Limited focus from larger media players Limited marketing services providers for advertisers Townsquare Markets Stable markets with lower economic volatility and stabilizing institutions such as universities, military installations and state capitals The Heartland is as much a mindset as it is a geographical definition, and many of our brands are significant influential institutions in this landscape that can help shape trends Townsquare 6

Local Marketing Solutions Overview Providing broadcast and digital products and solutions to businesses in small and mid-sized markets Radio 317 radio stations across 67 small to mid-sized markets Reach approximately 12+ million listeners (1) #1 or #2 share of radio revenue in 65 of 67 markets Strength in Country, News/Talk/Sports and Rock formats Live and local personalities with strong ties to the community 51 top-rated live and local morning shows (2) Over 90 heritage stations with average market leadership of at least ten years Select LMS brands Local Digital 325+ local, community websites Reach approximately 13 million UVs (3) per month with locally relevant, engaging content populated by local personalities and editors Digital marketing solutions offering, Townsquare Interactive, provides ~12,400 (4) customers with a total web marketing presence SEO and mobile optimized websites, hosting & listing services, social media & reputation management Proprietary digital programmatic platform, Townsquare Ignite, provides precision customer targeting solutions Proprietary mobile radio app, radiopup, reaches our audience on the go (~1 million downloads to date) 2017 net revenue and Adjusted Operating Income of $349 million and $114 million, respectively Townsquare 7 Note: Please refer to page 2 for definitions of non-gaap measures. (1) Represents the average of Townsquare s Spring 2017 and Fall 2017 nationwide cume, P12+ M-Su 12a -12a, per Act 1 Systems (based on Nielsen data). (2) Represents morning shows that are ranked first in-format based on Nielsen s A25-54 ratings. (3) Represents average monthly global unique visitors in 2017 per Google Analytics. (4) As of December 31, 2017.

Ad Solutions Ad Products Townsquare Everywhere: An And vs. Or Offering Our offerings complement, rather than displace, one another, from both the advertiser and audience perspective Our audience can utilize each of our content offerings Local Radio Local Digital Local Live Events Programmatic Our customers can reach consumers across multiple or discrete platforms Digital Marketing Solutions Data Solutions Analytics Solutions Townsquare 8 Subscription Revenue

Financial Strengths Attractive Growth 3.9% / 5.2% FY 2017 / Q4 2017 Local Marketing Solutions Net Revenue Excluding Political Growth Strong Margins 19.2% 2017 Adjusted EBITDA Margin Solid Capital Structure 5.6% Weighted Average Interest Rate (1) No Maturities until 2022 Healthy Free Cash Flow ~$41 million 2017 Adjusted EBITDA Less Interest, Capex and Taxes / $1.50 Per Share (2) Shareholder Return $0.075 Quarterly Dividend Per Share, $0.30 Per Share on an Annualized Basis (3) Note: Please refer to page 2 for definitions of non-gaap measures. (1) Based on current LIBOR rates as of March 12, 2018. (2) Based on 27.5 million shares and warrants outstanding as of March 10, 2018. (3) Townsquare s Board of Directors approved a quarterly dividend payment of $0.075 per share, payable on May 15, 2018 to shareholders of record as of April 2, 2018. Townsquare 9

FY 2017 Earnings Call Highlights 2017 net revenue was nearly flat (-0.4%) excluding political revenue, and declined 1.7% in total, compared to the prior year 2017 Local Marketing Solutions net revenue increased 1.9%, and 3.9% excluding political revenue (5.2% excluding political revenue in Q4 2017) 2017 Entertainment revenue decreased 8.6% Acquired 6 radio stations and 2 FM translators in Pittsfield/Berkshires, MA and executed an agreement to acquire WOUR-FM in Utica, NY on February 15, 2018 Represent buyer multiples of <6x EBITDA Announced initiation of quarterly dividend $0.075 per share payable on May 15, 2018 to shareholders of record as of April 2, 2018 Repriced Term Loan Facility, representing approximately $750,000 annualized interest expense savings (1) Repaid $6.7 million of Term Loan Facility in March 2017 2018 excess cash flow sweep of $9.5 million to be paid in March 2018 5.2x net leverage as of December 31, 2017 Note: Please refer to page 2 for definitions of non-gaap measures. 1. On February 8, 2017, repriced Term Loan Facility by reducing applicable interest rate by 25 basis points, from LIBOR + 325bps to LIBOR + 300bps. Townsquare 10 10

Balance Sheet and Liquidity Update Capitalization (12/31/2017) $ in millions Maturity Pricing Cash $65.3 Revolver ($50 million) $0.0 2020 L +250bps Term Loans 291.9 2022 L +300bps, 1% Floor Capitalized Obligations 0.0 Total Secured Debt $291.9 Senior Unsecured Notes 280.1 2023 6.500% Total Debt $571.9 Secured Debt / 2017 Adjusted EBITDA (1) 3.0x Total Debt / 2017 Adjusted EBITDA (1) 5.9x Net Debt / LTM 2017 Adjusted EBITDA (1) 5.2x ~$115 million liquidity: $50 million undrawn revolver and ~$65 million cash Note: Please refer to page 2 for definitions of non-gaap measures. 1. Adjusted EBITDA for the twelve months ended December 31, 2017 was $97.2 million. Townsquare 11

Capital Allocation Priorities After taking into account our debt and dividend obligations, Townsquare has the following capital allocation priorities Invest in organic growth opportunities Prioritize high ROI investments in Local Marketing Solutions segment, where we have a sustainable competitive advantage Drive ratings and revenue share of local broadcast brands Continue to support growth opportunities in Townsquare Interactive and Townsquare Ignite Continue to develop and test innovative new products across our local footprint Reduce Net Leverage Target medium to long-term net leverage of 4.0x Prudently Pursue Attractively Valued Acquisition Opportunities Focus on assets that have strong brands and leading market share positions Add to portfolio of attractive radio station clusters Augment the growth of our local digital and live events offerings Evaluate assets that provide natural extension to our core competency and support our mission Townsquare 12

Ownership and Shares Outstanding Ownership Shares Outstanding ($ in Millions) Townsquare s multi-class structure is driven largely by FCC considerations Others 32% Mgmt 5% MSD Capital 6% MSG 12% Oaktree Capital Management 46% Class B (high vote) and Class C (no vote) shares revert to Class A (1 vote) shares upon a sale (shares in millions) # of Votes Primary Holders Class A Common Stock 13.8 1 Public & MSG Class B Common Stock 3.0 10 Oaktree & Management Class C Common Stock 1.6 0 MSD Class A Warrants (1) 9.0 0 Oaktree Total Shares + Warrants 27.5 Note: Represents ownership as of March 10, 2018. (1) Each warrant is exercisable for one share of Class A common stock, at an exercise price of $0.0001 per share. The aggregate exercise price for all warrants currently outstanding is $898. Townsquare 13

Key Management Steven Price Executive Chairman Prior Experience Chairman & Chief Executive Officer, Townsquare Senior Managing Director at Centerbridge Partners and Spectrum Equity Investors, LP President and CEO of LiveWire Ventures President and CEO of PriCellular Corporation (sold in 1998 for $1.4bn) Joined TSQ Co-Founder Dhruv Prasad Co-Chief Executive Officer Executive Vice President, Live Events, Townsquare Vice President at Thomas H. Lee Partners, LP Associate at Spectrum Equity Investors, LP Co-Founder Bill Wilson Co-Chief Executive Officer Executive Vice President and Chief Content and Digital Officer, Townsquare President of AOL Media SVP, Worldwide Marketing at Bertelsmann Music Group 2010 Stu Rosenstein EVP & Chief Financial Officer 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) Co-Founder Claire Yenicay EVP, Investor Relations Associate at Oak Hill Capital Partners Analyst at Merrill Lynch 2011 Townsquare 14