02/14/2026 - 11:00am to 4:00pm
Are you searching for the ultimate New England winter running experience? The Martha’s Vineyard 20 Miler and Amity Island Relay is a premier athletic event held on February 14, 2026, known for its flat, fast, and incredibly scenic point-to-point course. Starting at the Steamship Authority in Oak Bluffs and finishing at the Town Hall in Edgartown, the race is a favorite for runners training for the Boston Marathon. Participants enjoy a route that winds through the island’s most iconic winter landscapes, offering constant ocean views and a tour of the rugged coastline.
For those who prefer a team effort, the Amity Island Relay allows two-person teams to split the 20-mile distance, making it a perfect winter getaway for friends and running clubs. Whether you are tackling the full distance or the relay, this event showcases the serene beauty of the islands in February. To streamline your planning and maximize value, we suggest staying on the Cape for easy ferry access.
Recover in Comfort—Stay Near the Starting Line
Finish the Amity Island Relay and head back to a warm, private home on the sand. Our beachfront properties in Dennis and Yarmouth offer the ideal retreat for post-race recovery with the ocean views you love.