Martha’s Vineyard is one of New England’s most well-known destinations, with out-of-towners and nearby locals flocking to the island each weekend. While it’s no longer a hidden gem, it still makes for a great jaunt from many East Coast cities. Thanks to Seastreak ferries, the island is now accessible from New York City, Boston, New Bedford, and Highlands, NJ. Here’s how to do it in a weekend.
Hotel: Lark Hotel’s Summercamp in Oak Bluffs. Relive your childhood camp days at this newly renovated Oak Bluffs hotel. Its modern-chic decor complements the classic gingerbread style architecture famous of the area. Play a round of ping-pong in the rec room or relax on the massive front porch. Summercamp is located less than five minutes from everything you would want to do in Oak Bluffs, as well as the ferry dock, bike rental shops, and tons of restaurants. The hotel even gives you a “Camp Guide” book with suggested itineraries and restaurant recommendations.
Friday: Arrive on a late morning ferry and leave your bags at the hotel if you aren’t able to get early check-in. Head over to Anderson’s Bike Rentals for their 3-day bike special ($95 for two bikes). Cycle from Oak Bluffs to Edgartown (around 7 miles one way) and walk Edgartown’s downtown for shopping, or stop for a drink at any of the bars or restaurants. Watch the barges float between the town and Chappaquiddick Island, or Chappy.
Return back to Oak Bluffs before dark and park your bikes at the back of the hotel on their bike rack. Head out for dinner and drinks at any of the Oak Bluffs waterfront restaurants. Make sure to get a midnight snack from Back Door Donuts, the line is long even at 12 a.m.!
Saturday: Bike three miles along the beach bike path to Joseph Sylvia State Beach and set up camp for the day. Rent a kayak or paddle board for an hour through Island Spirit Kayak, located across the street. Once you’ve had enough sun, bike just two more miles down the road to Bad Martha Farmer’s Brewery for an afternoon treat. Don’t have too many though, because you’ll need to bike back to Oak Bluffs, about five miles away. To catch the sunset you’ll need to give yourself some time to get to the other side of the island to Menemsha Beach in Chilmark. Call ahead to Larsen’s Fish Market and order some seafood takeout to eat on the sand. Menemsha is accessible via the public buses (VTA), or cabs will take you there for a flat rate.
Sunday: Return your bikes and take the bus to either Lighthouse Beach or South Beach in the morning and spend the day relaxing before taking an evening ferry. If you’re up for it you can bike the 10 miles and take the bus back, each VTA bus has bike racks slots on the front. Pick up sandwiches at Skinny’s Fat Sandwiches to take with you, or stop in Edgartown on your way back for a late lunch.
Extra Day: Return to any of the beaches for another full day in the sun, shop in downtown Oak Bluffs or Edgartown, or take the ferry 527 feet and explore Chappy Island.
Bar & Restaurant Recommendations
- Garde East, Vineyard Haven
- Atlantic, Edgartown
- Off Shore Ale Co., Oak Bluffs
- Nancy’s, Oak Bluffs
- Lola’s, Oak Bluffs
- The Seafood Shanty, Edgartown
- Skinny’s Fat Sandwiches, Edgartown & Oak Bluffs
- Larsen’s Fish Market, Chilmark
- Martha’s Vineyard Gourmet Coffee & Bakery, Oak Bluffs
- Bad Martha Farmer’s Brewery, Edgartown
- Joseph Sylvia State Beach, Oak Bluffs
- Lobsterville Beach, Aquinnah
- Menemsha Public Beach, Chilmark
- Lighthouse Beach, Edgartown
- Katama Beach (South Beach), Edgartown
More from SmarterTravel:
- Don’t Miss the Boat to Martha’s Vineyard
- 8 Secret American Islands You’ve Never Heard Of
- Seafood Shacks Worth the Drive
We hand-pick everything we recommend and select items through testing and reviews. Some products are sent to us free of charge with no incentive to offer a favorable review. We offer our unbiased opinions and do not accept compensation to review products. All items are in stock and prices are accurate at the time of publication. If you buy something through our links, we may earn a commission.