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Insider’s Guide to Martha’s Vineyard Activities

20 Year-Round Martha’s Vineyard Activities Suggestions

Shoulder-Season Martha’s Vineyard Activities

  1. Walk the beaches. Many beaches, especially ‘Up-Island’ are closed to the public during the summer months. Take this opportunity to enjoy these unspoiled stretches with no one else around! Keep your eye out during the winter for snowy owls that have been spotted on Beach Road between Edgartown and Oak Bluffs.
  2. Shop. The winter is a great time to pick up bargains. Take advantage of the winter wind-down to grab that island keepsake at a discount, or shop for next season as stores clear out for next summer.
  3. Get back to nature. Wonderful hiking trails abound – from gentle strolls to energetic hikes. Plus, the views can be stunningly different with less (or no!) foliage to obscure the expanse. See what new spots you can discover.
  4. Eat. Tons of great restaurants are open year round all over the island. Many run special theme nights or discount nights. Check with us for the latest offerings. For microbrew fans, Offshore Ale Co. is an option for tastings and tours.
  5. Pamper yourself. Enjoy a massage or facial. Relax, unwind, de-stress. Onsite here at Vineyard Square, Sea Spa Salon is offering great daily discounts on treatments.
  6. Support a community event. Locals come out to play and support their favorite causes in the winter.  Every week there boasts an array of events to support many Island charities. Join in and enjoy the local color!
  7. Catch a movie. In addition to the year round big box office releases at Edgartown Cinema,  you can enjoy movies and events from the MV Film Society at their Tisbury marketplace location. Sometimes a documentary, sometimes a foreign film – always something a little off the mainstream.
  8. Gallery Stroll. Enjoy the local art scene at a quieter pace, chat to the gallery owners about the collections while they have time to chat back. Then hit one of the many craft or artisan fairs at this time of year.
  9. Work out. Jog through the quiet streets. Take a yoga class. Spin, hit the Y for some Zumba or other fun class before checking out their pool and other great facilities. Recommit to your workout with a fun getaway to our nearby island!
  10. Disconnect and reconnect. Turn off the phone (yes we said it!) and reconnect with a loved one. The quiet of the Vineyard in winter is the perfect atmosphere to rediscover why you fell in love.

In-Season Martha’s Vineyard Activities

  1. Stroll (or Jog) North Water Street. Beautifully renovated captains’ homes date to when Edgartown was a major whaling port called Great Harbour. Don’t miss the Emily Post House garden at 34 Fuller Street. The famous advocate of all things mannerly summered there from 1927 until her death in 1960. She wrote often of her garden, especially her Dahlias, which are still lovingly tended by the current owners.
  2. Climb Edgartown Lighthouse. Saunter down to Edgartown Lighthouse, take a tour and climb to the top for the best view of Edgartown Harbor.
  3. Tour Chappaquiddick’s East Beach. Ride the On-Time Ferry and meet the van on “the Chappy side.”  Take an over-sand vehicle tour of beautiful East Beach, learn about the natural history of this unique location and tour Cape Poge Lighthouse – the lighthouse that visitors rarely see as it’s ONLY accessible by beach vehicle or boat! Talk about “insider!”
  4. Be a Jaws Groupie. “It’s only an Island if you look at it from the water,” is Brody’s infamous line from Jaws, which was filmed on Martha’s Vineyard in 1974.  Ask us for a Jaws tour map and we’ll point out the most recognizable movie locations. Then, take Brody’s advice and get out on a boat. Options abound – from a short ride around the harbor on a launch to a full-day adventure on the high seas. See some of our suggestions on our Beaches and Boating page.
  5. Revel in Beach Nightlife. Ride out to Menemsha, join the throng on the beach, and picnic in the stunning light of the setting sun. Revel in the party atmosphere as children play, impromptu jam sessions break out, music fills the air, and new friends are made. Let us call ahead to Larsen’s Fish Market to arrange a take-out New England Clambake of lobster, clams, corn on the cob and all the fixin’s.
  6. Hop on a Bus. If this is your first Martha’s Vineyard visit (or even if it’s not), we highly recommend a bus tour to hit island highlights. Our favorite is the brightly painted Martha’s Vineyard Sightseeing Bus. The company offers a 2½-hour tour with a ½-hour stop at the Aquinnah Cliffs and Gay Head Lighthouse. The Cliffs are a protected National Historic Landmark and the lighthouse was made from clay bricks culled from the site. Martha’s Vineyard Historical Society on School Street displays the lighthouse’s original 1856 Fresnel Lens. You’ll learn a lot of Island lore (as well as hear wonderful anecdotes from a great group of knowledgeable drivers!)
  7. Explore Oak Bluffs. As eclectic as Edgartown is refined, Oak Bluffs offers tons to keep you entertained as well as fascinating history. Don’t miss the ‘Gingerbread Cottages’ in the Campgrounds.  These brightly painted, ornately carved cottages were built by the Methodist Church campers during the mid 1800’s.  The Tabernacle, the physical and spiritual center of the Campgrounds, is on the National Register of Historic Places and is still home to weekly church services in July and August, and host of cultural events throughout the summer.
  8. Ride the Carousel. Another Oak Bluffs must-see is the Flying Horses Carousel. Housed in a dark red building near the Steamship Authority terminal, it’s the oldest operating platform carousel in America.  Don’t forget to reach for the Brass Ring to win a free ride (you’ll understand once you get there).
  9. Feed Your Inner Chocoholic. Make a pilgrimage to a little cottage in Chilmark – home to decadent Chilmark Chocolates. These handmade chocolates are one of the Island’s best-kept secrets. Only available at 1 or 2 locations on Island (nope – no website!), you queue up (there’s ALWAYS a line), and shuffle through the tiny store to pick out your selections. Trust us – it is worth it. Our weakness is the milk chocolate butter crunch (which is featured on the Snowball Dessert at Chescas).
  10. Relax! That’s our Number One tip. Give in to the quieter island pace, reconnect and enjoy. Stop by the concierge desk if you need help or ideas.

Guest Reviews

“Everything at Vineyard Square was excellent – the staff were friendly and accommodating and the location could not be better for getting around downtown on foot. The home made breakfast every morning was delicious and the access to bikes was an added bonus. Cannot recommend it enough!”

Sheila T

“We enjoyed our stay very much. The location is perfect – close to everything in town. We chose a cozy room and it was quite small, but we got used to it and enjoyed spending time on the spacious porch in the early morning and late afternoon. The breakfast selection was amazing and we enjoyed eating on the patio outside, weather permitting. The staff was very friendly and helpful and were able to book us dinner reservations at a popular restaurant. This was the second time we have stayed at Vineyard Square and we would definitely stay there again.”

Gloria N

“My sister and I visited Martha’s Vineyard and had a lovely stay at the Vineyard Hotel and Suites. The accommodations were excellent and staff were very attentive. Enjoyed the deluxe continental breakfast. The hotel was located in the perfect location. All shops and restaurants were in close proximity.”

Lisa M

“We spent 4 nights in a beautiful suite and loved the location, the room, and the experience. Everything is walkable, the service was good, they had a nice complimentary breakfast, the front desk was accommodating (umbrellas, pillows, waters, etc) and of all the hotels / inns we saw, we felt like this was an excellent choice. Parking is free but is a block away (which is not unusual in the heart of town). Would absolutely stay here again!”

Blake T

“My stay at the Vineyard Square Hotel & Suites was a blast! The hotel offered everything from complimentary homemade breakfast (even meeting the chef) to friendly staff. The location is excellent, and I highly recommend taking the complimentary bikes for a trip to Oak Bluffs and enjoying many fabulous restaurants only 500 ft away!”

Peter T

“Everything at the Vineyard Square Hotel & Suites was excellent – from the delicious homemade croissants to the easy access bikes. The location is perfect and the staff are all friendly and accommodating. The perfect place to stay on Martha’s Vineyard!”

Sheila M

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