MV Winter Classic 20 Miler
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Event overview
The MV Winter Classic and Amity Island Relay takes place on February 14, 2026 in Vineyard Haven, MA. The event includes the following distances:
- 20 miles
- Amity Island Relay - two 10-mile legs
The course is USATF certified (MA17039JK). Proceeds benefit several Island youth programs; participating local organizations and teams assist with volunteers and receive a share of event proceeds.
Course and race information
The race is a point-to-point route that starts in front of the Steamship Authority Vineyard Haven terminal and finishes in Oak Bluffs. The course is mostly flat with some rolling hills and passes through three Island towns. Notable route features include the Gingerbread Cottages of Oak Bluffs, a barrier beach road along Sengekontacket Pond, a section of Edgartown’s farming community, and a finish through Manuel F. Correllus State Forest.
Course support includes accurately placed mile markers and nine water stations. Post-race provisions include bagels, fruit, treats from Morning Glory Farm, coffee, and hot chocolate. There are multiple award levels; every participant receives a finisher medal and an official event t-shirt. The race has a 4-hour course cutoff (12-minute-per-mile pace); runners who continue after the cutoff do so without aid from volunteers or police. Visit the organization's website for the most recent information.