MV Winter Classic 20 Miler

FEB
14
2026
Run the MV Winter Classic and Amity Island Relay in Vineyard Haven MA on February 14 2026. Pick the certified 20 mile course or a two person relay of 10 mile legs and enjoy scenic island roads, gingerbread cottages and a forest finish.
Sat 14 Feb 2026
20 miles

Always double-check with the organizer's website! This page may contain affiliate links.

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.

20 mi
Amity Island Relay (2x10 Miles)
20 mi
20 Miles

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