Best 165 things to do in Dartmouth, MA

Schedule island-wide kayak delivery and pick up

Build paddling skills at any level with a private lesson

Rent a paddleboard for 24 hours at State Beach in Oak Bluffs

Paddle open-ocean routes to remote spots with guides on Martha’s Vineyard

Paddle at sunrise with breakfast and coffee included

Start your day with a beginner-friendly paddle board fitness class

Rent a kayak or paddle board for 1–3 months with free delivery

Paddle Sengekontacket Pond with a private guide tailored to your group

See Plymouth Harbor highlights with live narration from an expert crew

2-hour Plymouth Harbor party cruise with DJ, onboard bar, and landmark views

Nighttime harbor cruise with ghost stories and Plymouth history

Sail into the Plymouth sunset with live music, appetizers, and unlimited drinks

Join a pirate crew mission with treasure maps and water cannons

Haul lobster traps and meet Plymouth Harbor sea life in 1 hour 15 minutes

Build your own ice cream sundae on a 75-minute Plymouth harbor cruise

Savor brunch and mimosas while cruising Plymouth Harbor

Cruise Cape Cod’s outer beaches with a spotter pilot to look for great white sharks

Reserve a performance road bike in advance for your Edgartown ride

Cruise the island on a pedal-assist Townie e-bike with 3 speed settings

Cruise to town or the beach on a comfy 7-speed Townie

Cruise comfortably on a hybrid commuter bike with helmet and lock included

Cruise the island on a Specialized Como e-bike with pedal assist

Rent a premium dual sport bike for smooth riding on dirt roads and pavement

Ride Martha’s Vineyard trails on a Trek hardtail mountain bike