MV Winter Classic & Amity Island Relay Tisbury, MA   Feb 14, 2026

The MV Winter Classic and Amity Island Relay is a must race for die-hard runners of many levels. From highly competitive athletes looking for a test of their Boston and spring marathon readiness, to dedicated recreational runners seeking to extend the length of their monthly long-run, this race offers the chance to combine a visit to one of the East Coast’s most beautiful shore communities with a race on a fast, USATF certified course. Not quite up to the 20 mile challenge? Grab a partner and enter the Amity Island Relay (2×10 miles)!

​The course is mostly flat, with some rolling hills, and circles through the varied terrain of three Island towns. Starting at Vineyard Haven Harbor, runners pass by the historic Gingerbread Cottages of Oak Bluffs, work their way along a barrier beach road that separates Nantucket Sound and the 700 acre Sengekontacket Pond, cross a section of Edgartown’s farming community, and finish back in Oak Bluffs with a trek through the Massachusetts Department of Conservation & Recreation’s Manuel F. Correllus State Forest.

Be prepared for all New England has to offer. Some years are bright and sunny, others are windy and damp, and of course there is always a chance of snow! The harsher the weather, the greater the tale!