Ready to take your next vacation above and beyond?

Let us know how you live your life above and beyond by filling out the form for your chance to win two Herschel duffle bags $250 travel gift card of your choice (i.e. gas, Hilton, Marriott, Delta, Airbnb etc.). 

One winner will be selected each week. If you are selected as a winner, we'll contact you with the information provided.

MassMutual Ascend Life Insurance Company (“MassMutual Ascend”) will award a $500 prize to each winner of a weekly drawing to be held from October 7, 2022, to December 30, 2022, subject to these rules and conditions.


No purchase or other consideration is required to enter.  To enter, simply complete the registration form our website,  The registration form must be received no later than the day before the drawing.  Incomplete entries may be disqualified.


An entry that is not drawn one week will carry over to the drawings for subsequent weeks.  While you may enter multiple times, you (or any person sharing your email account) may win only once.  Odds of winning depend upon number of entries received, and will decline over the duration of the period of the drawings.


The following are not eligible to win: (1) Employees of MassMutual Ascend or an affiliated company; (2) individuals under age 18, (3) individuals without a valid email address; (4) individuals who are not lawful U.S. residents; (5) individuals who are entering in the capacity as agent, attorney-in-fact, trustee, or other representative for some other person; (6) corporations, partnerships, LLCs, and other non-natural persons, (7) individuals who are subject to pending felony charges, or who are incarcerated on the date of the drawing; (8) individuals who have delinquent child support, spousal support or alimony, or tax payments; (9) individuals who are subject to backup withholding; (10) individuals who are subject to a judgment lien; (11) any entries determined by MassMutual Ascend, in its sole judgment, to have been generated by a script, macro, or by use of automated devices; or (12) any person determined by MassMutual Ascend, in its sole judgment, to have tampered with the registration process or the operation of this drawing or website, or to have annoyed, abused, threatened, or harassed any other entrant or MassMutual Ascend or any of its representatives.


Drawings may be made in the manner determined by MassMutual Ascend, and may be electronic.  Winners will be notified by email.  An undeliverable email, an ineligible entry, a failure to provide requested documentation within the specified time, the making of any false statements, a failure to claim a prize within 30 days, an undeliverable prize check, or failure to cash a prize check within 90 days, will be grounds to forfeit the prize in the sole discretion of MassMutual Ascend.  If a prize is forfeited, it will not be re-awarded.  Winner is solely responsible for all taxes on the prize.


By entering in this drawing, entrants agree to MassMutual Ascend’s use of their personal information for both online and offline direct marketing purposes.  For details [and to opt-out], visit MassMutual Ascend’s privacy policy at [] and []  Winning constitutes permission (except where prohibited by law) to use winner’s name, hometown, prize won, and photograph (all at MassMutual Ascend’s discretion) for future advertising or publicity in any and all media now or hereafter devised in perpetuity, without additional compensation, notification, or permission.


Each entrant agrees that MassMutual Ascend and its officers, directors, agents, representatives, and employees are not responsible for: (1) lost, late, misdirected, damaged, stolen, altered, garbled, incorrect, incomplete, or delayed entries, all of which will be void; (2) problems related to technical malfunctions of electronic equipment, computer online systems, servers, or providers, computer hardware or software failures, phone lines, and a failure of any entry to be received or retained by MassMutual Ascend on account of technical problems, traffic, congestion on the internet or the website, or for any other technical problems including telecommunication, miscommunication, or failure, and failed, lost, delayed, incomplete, garbled, or misdirected communications which may limit a entrant’s ability to participate in this drawing; or (3) any other errors or malfunctions of any kind, whether network, printing, typographical, human, or otherwise relating to or in connection with the drawing, including, without limitation, errors or malfunctions with may occur in connection with the administration of the drawing, the processing of entries, or the announcement of the winner.  Each entrant waives all rights to claim, punitive, incidental, or consequential damages, or any other damages, including attorneys’ fees, or to have damages multiplied or increased.  All issues and questions concerning the construction, validity, interpretation and enforceability of the drawing rules, or the rights and obligations of entrants and MassMutual Ascend in connection with this drawing, shall be governed by, and construed in accordance with, the substantive laws of the State of Ohio.


MassMutual Ascend reserves the right, at its discretion, to reschedule the drawings or the entry and/or end dates, to modify the entry procedures, or to cancel future drawings.  MassMutual Ascend reserves the right to modify, suspend, or terminate the drawings in the event the registrations become infected by a computer virus or is otherwise technically impaired, and to cancel or suspend the drawing in its entirety should tampering, unauthorized intervention, fraud, technical failures, or other causes corrupt the administration, security, fairness, or integrity of the drawings.  If terminated, MassMutual Ascend may, in its discretion, determine one or more winners using all non-suspect, eligible entries received up to time of cancellation.


Any attempt by an entrant to deliberately damage any website or undermine the legitimate operations of the drawing is a violation of criminal and civil laws. Should such an attempt be made, the MassMutual Ascend reserves the right to seek damages from any such entrant to the fullest extent permitted by the law and to refer such entrant to law enforcement officials.


Drawing subject to all federal, state, and local laws and regulations. Void where prohibited by law.