MV Winter Classic 20 Miler

FEB
14
2026
Run a scenic point to point 20 mile across Martha's Vineyard or team up in a two person 2 x 10 mile relay, finishing in charming Oak Bluffs. Enjoy coastal views, rolling hills, post race food and a finisher medal and shirt.
Sat 14 Feb 2026
20 miles 10 miles

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Event overview

The Martha's Vineyard 20-miler and Amity Island Relay is a point-to-point road race on Martha's Vineyard. It is USATF certified (MA17039JK) and offers a solo 20-mile option plus a two-person relay. The race starts in front of the Steamship Authority Vineyard Haven terminal and finishes in Oak Bluffs. Weather on race day can vary from bright and sunny to windy, damp, or snowy.

Distances

  • 20 miles
  • Amity Island Relay - 2 x 10 miles

Course and logistics

The course is mostly flat with some rolling hills and passes through parts of three Island towns. The route goes by the Oak Bluffs Gingerbread cottages, along a barrier beach road beside Nantucket Sound and the 700-acre Sengekontacket Pond, crosses a section of Edgartown farming area, and finishes with a section through the Manuel F. Correllus State Forest.

Mile markers are placed accurately along the route, and there are nine water stations. Organizers provide post-race food including bagels, fruit, and treats from Morning Glory Farm, plus coffee and hot chocolate. There are multiple award levels; every finisher receives a medal and an official race t-shirt.

A race cutoff time of four hours applies (based on a 12 minute per mile pace). Runners who cannot complete the course within that time continue at their own discretion without aid station or course support. Questions are handled by the event organizer. Visit the organization's website for the most recent information.