Tips and trails for Coastal Cycling in Massachusetts
Ride the Shoreline Like a Pro
Massachusetts is a haven for cyclists who crave ocean views, salty breezes, and historic seaside towns. Whether you're a weekend rider or training for a long-distance tour, the Bay State’s coastline offers stunning routes and unique cycling challenges. Follow these expert tips to ride the shoreline like a pro.
You picked Best Coastal Cycling Routes in Massachusetts
Planning your ride starts with choosing the right route. Massachusetts offers a variety of coastal bike paths, each with its own vibe.
Martha’s Vineyard Bike Paths: 44+ miles of interconnected, paved trails linking towns like Oak Bluffs, Edgartown, and Vineyard Haven. Ideal for all levels, these flat, scenic paths run alongside beaches, forests, and historic sights—perfect for casual rides, family outings, or a full-island too.
Southern Shore Ride (Oak Bluffs): Historic streets, rocky shores, and postcard-perfect. harbors.
Byways: Combines seaside village charm with stunning coastal views, weaving through historic towns, lighthouses, farmland, and oceanfront stretches—from Oak Bluffs to Aquinnah.
Full-Island Perimeter Loop (60+ miles)
Route: Vineyard Haven → Oak Bluffs → Edgartown → Katama → South Road → Aquinnah → Chilmark → West Tisbury → Vineyard Haven
Highlights: Ocean views, Gay Head Cliffs, rolling up-island terrain
Skill Level: Advanced
Notes: Mix of bike paths and shared roads; limited services between Aquinnah and Chilmark—stock up on water/snacks
Katama–South Beach–Edgartown Loop (20–25 miles)
Route: Oak Bluffs → Edgartown bike path → Katama → South Beach → Edgartown → Oak Bluffs
Highlights: State Beach views, farm fields, coastal breezes
Skill Level: Intermediate to Advanced
Notes: Mostly flat; excellent for tempo training with low traffic
Beach-to-Beach Loop (30 miles)
Route: Vineyard Haven → State Beach → South Beach → Long Point Wildlife Refuge → Lambert’s Cove Beach
Highlights: Cross-island ride with beach detours and photo ops
Skill Level: Intermediate to Advanced
Notes: Pack a lock and swimsuit for quick dips!
