As it is the largest New England island, with its hundred square-mile stature, Martha’s Vineyard is brimming with possibilities and activities for all to enjoy. The several towns on island all have starkly different personalities from one another, from the (slightly) urbane Oak Bluffs to the quiet fishing villages in Chilmark’s Menemsha. However, all towns are riddled with hints of its whaling past, with its five distinctive lighthouses and several ports and fishing markets. It may seem overwhelming on what exactly to get done on the Vineyard, so the Harbor View is providing a perfect 36-hour weekend on island. Arrival by plane or ferry is simple. For a full list of ferries to the island, look here.
1. Farm-to-Table-to-Beach, 2 p.m.
After hopping off the ferry, grab a bite to eat at the farm-to-table Scottish Bakehouse on State Road in Vineyard Haven. Choose one of their spectacular grilled sandwiches, from the Portobello wrap spinach, red onion, goat cheese) or their FBLT (frickin’ bacon lettuce tomato) and one of their renowned baked goods (personal favorite: gluten-free cheesecake bite). Then continue on to Joseph Sylvia State Beach in Oak Bluffs. There, either relax and enjoy your sweets, or get more active by renting kayaks or paddleboards from Island Spirit Kayak, located right on the beach! Walk-ins welcome. Also for movie buffs, it’s a great spot to get a good look at the infamous “Jaws” bridge.
2. Show-Shopper, 4:30 p.m.
There’s more to Martha’s Vineyard Fashion than just Vineyard Vines and salmon-colored pants. Explore the boutique shops Edgartown has to offer. At Slate, a new store on the island, find gorgeous nautical themed clothing. At In The Pink find the classic, preppy Lily Pulitzer dress for all your Vineyard cocktail party needs. Walk next door to Backwater Trading Company, and pick up one of the East Wharf Bags, which are made entirely from recycled sails. They come in all different sizes, from wristlets to wine totes to beach bags ($45-$150). After, stroll down Main Street and turn left onto Dock Street and go into Portobello Road. Open from 10am to 6pm, this store is inspired by the London Flea market of the same name, and offers an eclectic collections of toys, books, signs, and thoughts. Stop by Edgar for high-end Vineyard clothing and cutesy, swan shaped pool floats.
3. Harbor Views, 6:30 p.m.
Stop for a cocktail or a seafood appetizer at Henry’s located in the Harbor View, a classic bar and restaurant that overlooks Edgartown Harbor, where you can look at all the boats coming in. Yachts and sailboats tend to park right in the harbor which is excellent for marveling purposes. Order the Chatham Mussels ($19) or some New England Cheeses ($16) for a snack before going out. Order any one of their signature cocktails such as The Lightkeeper ($13, a drink made with Grey Goose vodka, Fresh Lemonade, St. Germaine topped with soda water on the rocks) or The 125, the hotel’s 125th anniversary drink!
4. Light up l’étoile, 8 p.m.
One of the longest running chef owned and operated restaurants on the island, l’étoile is a French restaurant that offers an extensive three course meal, while maintaining a vineyard feel by using native ingredients. This restaurant offers indoor and outdoor seating options, with lanterns to light up the night. Some of the standout eating options include Hudson Valley Duck Foie Gras ($26), Prime Chesapeake Bay Soft Shell Crab ($17), and Striped Bass Fillet on Spring Sweet Pea Risotto ($39). With drinks, expect to pay around $140 – a good deal for an exquisite meal.
5. Ice Cream, 9:30 p.m.
Scoop Shack is the new kid on the block, in terms of ice cream on the Vineyard, and has proven to be the best. With their special flavors (mint green tea with honey and ginger snaps) and modern takes on classics (mint chip, cookie dough), it’s no wonder why there’s always a line. But fear not, for it moves quickly. $4.50 for a single scoop, and no need to feel guilty for being a cup person instead of a cone person, as they have eco-friendly spoons. .25 cent taffy fills huge buckets in the store of every color and flavor, as well as other old-timey candy, fills the shelves. The ice cream is homemade on the Vineyard. Probably (definitely) the best ice cream on island.
6. Early Birds, 8 a.m.
Only having 36 hours to spare, an early start is the right start. If you’re up for it, watch the sunrise as the Harbor View has one of the best views on the island. After that, stretch out and work out with the Harbor View’s yoga on Great Lawn to get a good jump on the day. The best part? It’s free to all Harbor View guests.
7. Nooks and Crannies, 9:30 a.m.
After showering off that workout, head back into town and find Behind the Bookstore. Which, yes, is in fact behind Edgartown Books. A cute nook, with tarps overhead produces a cool shade for basking. Decorated with flowers, it creates a calming ambiance. Breakfast is served from 8 a.m – 12 a.m. and offers simple and elegant options. Go for something simple like the House-made Granola and Yogurt ($7, with berries $9) or something more robust like the House-cured Salmon on Homemade Rye ($13.50) or the Fried Egg BLT with avocado ($11).
8. (Farm) Stand of Ovation, 11 a.m.
Head on over to West Tisbury Farmer’s Market, to pick up locally grown foods and goodies for lunch. Only open in the mornings on Saturday’s and Wednesday’s, this is a necessary stop. The market has everything for the perfect picnic from breads and veggies, to smoked fish and meats and maybe even an alpaca wool picnic blanket! Look here for more information on the farmer’s market.
9. Moooving On, 12:30 p.m.
From there, head up island to Menemsha Beach. It’s a beautiful drive with water views, and a good chance to experience a small portion of the vast beauty, which is Martha’s Vineyard. Make a stop on the way to the beach at Grey Barn and Farm to taste some of the best cheese on island, if you forgot to buy some at the farmer’s market, and meet some cute dairy cows while you’re at it.
10. Blue Water, 2:30 p.m.
Enjoy one of the prettiest beaches on island, Menemsha Beach. Look out at the bright blue water, which is reminiscent of Bermudian shores which can be wavy or flat, depending on the day. Enjoy your farmer’s market lunch and lounge. Bring along a book or pay rock bocce – since stones are plentiful on the beach.
12. Lazy Lobsters, 6:30 p.m.
For dinner, enjoy some of the best seafood on island. The Home Port in Menemsha serves seafood caught in local waters, by local fishermen. It doesn’t get much more Vineyard than that. This particular restaurant is known for two things, which are must-orders. The first being their world class New England Clam Chowder ($8) and their Menemsha Lobsters which are market price. For an extra few bucks, the chefs will crack the lobster for you, a meal fittingly titled the “Lazy Lobster.” The Home Port is especially conveniently placed for it offers a prime view of the world-famous Menemsha sunset, which can be enjoyed from your table. Alcohol cannot be purchased from the Home Port, as it’s located in one of the dry towns on the Vineyard – but fear not, it’s BYOB and they provide ice buckets and mixers.
13. Back Door Donuts, 8 p.m.
Scoot on over to Oak Bluffs to queue up for the best doughnut you’ll have in your life. By day, M.V. Gourmet Café and Bakery is an everyday bakery, but by night it transforms into Back Door Donuts. Back Door Donuts makes fresh donuts and pastries from 7:30 p.m. to 1 a.m. The thing to order here is the Apple Fritter, which is pretty cheap for being probably the best food you’ll have in your life.
14. Dance It Off, 9:00 p.m.
Start heading back home to the Harbor View, but stop again in Edgartown at The Port Hunter. Here live music is played almost every Saturday night, giving you a great opportunity to dance off that apple fritter. It’s a small joint so it’s perfect for smaller groups to hang out and dance off.
15. Lighthouse Grill, 10 a.m.
Voted “Best Brunch” by Boston Magazine, Sunday’s are a great day to be Harbor View Guests. At the Lighthouse Grill, which is open from 10 a.m. to 2 p.m., guests and islanders alike can enjoy a prime selection of delicious foods. The menu is not available online, because it changes every week. You can expect to see some old favorite like omelets and pancakes – but expect more than that. With a buffet component and a menu, all parties will be satisfied by this brunch.
16. Walk it Off, 11 a.m.
Walk off your brunch with a final walk around Edgartown. Check out the art of local vineyard artists in the lopsided, historical Old Sculpin Gallery. Grab a few slices of fudge or peanut brittle for your friends and family from Murdick’s Fudge. If you’re lucky, you might be able to catch them sculpting and making the fudge right before your eyes. The smell is overwhelmingly good.
The Harbor View