Townsquare Media, Inc.

UNITED STATESSECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549 ____________________________________

SCHEDULE 14A____________________________________

Proxy Statement Pursuant to Section 14(a) of theSecurities Exchange Act of 1934 (Amendment No. )

Filed by the Registrant xFiled by a party other than the Registrant oCheck the appropriate box:o Preliminary Proxy Statemento Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2))x Definitive Proxy Statemento Definitive Additional Materialso Soliciting Material under §240.14a-12

TOWNSQUARE MEDIA, INC.____________________________________________________________________

(Name of Registrant as Specified In Its Charter)____________________________________________________________________(Name of Person(s) Filing Proxy Statement, if other than the Registrant)

Payment of Filing Fee (Check all boxes that apply):x No fee requiredo Fee paid previously with preliminary materialso Fee computed on table in exhibit required by Item 25(b) per Exchange Act Rules 14a-6(i)(1) and 0-11

March 27, 2026

To the Stockholders of Townsquare Media, Inc.:

I am pleased to invite you to attend the 2026 Annual Meeting of Stockholders (the “Annual Meeting”) of Townsquare Media, Inc. (the “Company”), which will be held by virtual meeting format atwww.virtualshareholdermeeting.com/TSQ2026, on May 11, 2026 at 11:00 a.m. Eastern Daylight Time.

Information about the Annual Meeting, the nominees for election as directors and the other proposals to be voted on by stockholders is presented in the following Notice of Annual Meeting of Stockholders and accompanying proxy statement.

Whether or not you plan to attend the Annual Meeting, please promptly vote your shares in advance of the Annual Meeting using the methods described in the accompanying proxy statement. It is important that your shares be represented. We hope you can join us at the Annual Meeting on May 11, 2026.

Sincerely,

Steven Price

Executive Chairman of the Board of Directors

4 Manhattanville Road, Suite 107

Purchase, New York 10577

(203) 861-0900

NOTICE OF ANNUAL MEETING OF STOCKHOLDERS

May 11, 2026, 11:00 a.m. Eastern Daylight Time

The 2026 Annual Meeting of Stockholders (the “Annual Meeting”) of Townsquare Media, Inc. (the “Company”) will be held by virtual meeting format atwww.virtualshareholdermeeting.com/TSQ2026, on May 11, 2026 at 11:00 a.m. Eastern Daylight Time, for the following purposes:

(1)To elect two Class III directors named in the accompanying proxy statement to our Board of Directors, each director to hold office until the 2029 annual meeting of stockholders and until such director’s successor is duly elected and qualified, or until such director’s earlier resignation, retirement or other termination of service.

(2)To ratify the appointment of BDO USA, P.C. as our independent registered public accounting firm for the fiscal year ending December 31, 2026.

(3)To approve (on an advisory basis) the compensation of our named executive officers.

(4)To approve (on an advisory basis) whether an advisory vote on the compensation of our named executive officers should occur every one, two or three years.

(5)To transact such other business as may properly come before the Annual Meeting and any postponement(s) or adjournment(s) thereof.

Stockholders of record at the close of business on March 18, 2026 are entitled to receive notice of, to vote at and attend the Annual Meeting and any adjournment or postponement thereof. To attend the virtual Annual Meeting, you must demonstrate that you were a stockholder as of the close of business on March 18, 2026 or hold a valid proxy from any such stockholder. The Annual Meeting will be completely virtual, conducted via live webcast at the website above. On that website, you will be able to vote your shares electronically, view the list of stockholders entitled to vote at the meeting and submit questions during the meeting. Details regarding how to attend and participate in the virtual meeting are more fully described in the accompanying proxy statement.

Sincerely,

Steven Price

Executive Chairman of the Board of Directors

Purchase, New York

March 27, 2026

IMPORTANT NOTICE REGARDING THE AVAILABILITY OF PROXY MATERIALS FOR THE ANNUAL MEETING OF STOCKHOLDERS TO BE HELD ON MAY 11, 2026:

The accompanying proxy statement and annual report to stockholders are available free of charge at https://www.proxyvote.com

TABLE OF CONTENTS

TOWNSQUARE MEDIA, INC.

4 Manhattanville Road, Suite 107

Purchase, New York 10577

(203) 861-0900

PROXY STATEMENT

FOR THE ANNUAL MEETING OF STOCKHOLDERS

TO BE HELD ON MAY 11, 2026

Townsquare Media, Inc. (“Townsquare,” “Company,” “we,” “us” and “our”) has made this proxy statement (the “Proxy Statement”) and other materials available to you on the Internet or, upon your request, has delivered these materials by email or mail in connection with the solicitation of proxies by the Company’s Board of Directors (the “Board”) for use at the Company’s 2026 annual meeting of stockholders (the “Annual Meeting”). The Annual Meeting will be held in a virtual meeting format atwww.virtualshareholdermeeting.com/TSQ2026, on May 11, 2026 at 11:00 a.m. Eastern Daylight Time, and for any postponement(s) or adjournment(s) thereof. This proxy statement and the accompanying form of proxy will be mailed to stockholders on or about March 27, 2026.