A Weekend Guide to Martha’s Vineyard

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Just off the coast of Massachusetts lies Martha’s Vineyard - an island with storybook gingerbread houses, pristine beaches and charming historic towns. 

This quaint, New England summer destination caught my eye for a few years. With sailboats dotting the shoreline, fresh seafood at your fingertips and boutique shops galore, it seemed like the picturesque destination for our annual mother-daughter trip. So grab a glass of wine and get ready to follow our first adventure through Martha’s Vineyard. 

PSA: There are no vineyards on Martha’s Vineyard, but there are convertibles for rent, antique shops to explore, beach bonfires to be had and a slower pace to find.

WHEN TO GO 

If you don’t mind the crowds, summer is a popular season to visit Martha’s Vineyard. We opted to skip peak season and travel post-Labor Day. We fully expected cooler temperatures and fewer crowds but we were still greeted with sunshine, 80 degrees and plenty of other visitors late September. 

THE ROUTE

We had two legs of travel for this trip. We flew from Baltimore to Providence. Then took a 45-minute lyft to New Bedford to catch the Seastreak Ferry to Martha’s Vineyard. 

Seastreak offers multiple routes and schedules. Given the time of year, we were warned that the ocean could be a little rough in September, so we booked the shortest ferry ride possible to Oak Bluffs - our home base on Martha’s Vineyard. 

If ferries aren’t your cup of tea, you can also fly directly to the island

WHERE WE STAYED 

Oak Bluffs at The Oak Bluffs Inn - I highly recommend this inn. It’s in the heart of Oak Bluffs which makes it walkable to the ferry, shops, beaches and restaurants. With daily breakfast, cookies in the evening and a porch to relax on, it’s a tough spot to beat. The inn owners even threw us a beach bonfire on our last night and drove us to and from the ferry! 

OTHER STAYS THAT CAUGHT OUR EYE 

Oak Bluffs: Summer Camp and Pequot Hotel

Edgartown: The Hob Knob and The Christopher 

DAY 1: Travel Day with a Side of Shopping and Cocktails

Sights to See: New Bedford boutiques, Oak Bluffs boutiques, Sunset at Oak Bluffs Harbor 

Where to Eat: Tia’s Maria’s (New Bedford), Lobsterville (Oak Bluffs), Lookout Tavern (Oak Bluffs), Back Door Donuts (Oak Bluffs), The Red Cat (Oak Bluffs) - We weren’t able to eat at this one but it came highly recommended

Drinks to Clink: Lookout Tavern (Oak Bluffs), Lobsterville (Oak Bluffs) 

For our travel day, we took an early flight from Baltimore to Providence and then grabbed a cab to New Bedford, where our ferry was leaving. We had a few hours to spare so we popped some champagne at Tia Maria’s, had a bite of lunch and walked the cobblestone streets to check out the various art galleries and boutiques. Soon enough, it was time for us to set sail on our 2 o’clock ferry. 

Seastreak ferry terminal was easy to navigate, and within the hour, we were in Oak Bluffs. The Oak Bluffs Inn owner Erik picked us up and gave us a quick tour of the town before helping us settle in.

We dropped off our bags and walked down the street to the shop downtown for a couple hours. As we worked our way downtown, we made our way to Lookout Tavern for sushi and drinks on the balcony. With so many food options in the area, we hopped over to Lobsterville for a lobster grilled cheese on their patio to top off the evening and watch the sunset. 

If you have a sweet tooth like we did, make you way to Backdoor Donuts and order the Butternut Crunch - you won’t regret it. 

Day 2: Rent a Car & Explore the Island 

Sights to See: Oak Bluffs neighborhood, Morning Glory Farm, West Tisbury Farmers’ Market, Lucy Vincent Beach, Menemsha boutiques, Aquinnah Cliffs, Gay Head Light House, Vineyard Haven Boutiques  

Where to Eat: The Black Dog Dockside (Oak Bluffs), Morning Glory Farm, Menemsha Fish Market (Menemsha), The Beach Road (Vineyard Haven)

Drinks to Clink: Wine on Oak Bluffs Inn Porch, Beach Road (Vineyard Haven) 

For the first full day, we opted to rent a car to see as much as possible. And with the sunny forecast, we couldn’t pass up the opportunity to rent a convertible to zip across the island. 

Before hitting the road, we started the morning with a walk through the neighborhood and made our way to The Black Dog Dockside for a breakfast biscuit sandwich and coffee. The breakfast spot is next to A-A Island Auto Rental & MV Auto Rental, where we picked up our car for the day. 

With the keys in hand, our first stop was driving across Jaws Bridge - named after its appearance in Jaws, which was filmed at Martha’s Vineyard. Some visitors even make it a tradition to jump off the bridge as a summer rite of passage.

Passing through Edgartown, we made our way to Morning Glory Farm and West Tisbury Farmers’ Market to find artisanal souvenirs and treats.

We continued on to make our way to Lucy Vincent Beach to soak up the salt water and sunshine before heading to Menemsha for lobster rolls and shopping at the antique stores and galleries. 

Travel Tip: Menemsha is known for its lobster rolls and watching the sunset. Hundreds of people gather each evening for this tradition. 

Back on the road, Aquinnah Cliffs and Gay Head Lighthouse were our next stops. The views offered by the outlooks are truly breathtaking. 

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We took our time cruising back to Oak Bluffs and hit the porch for cocktail hour before heading to Vineyard Haven for dinner. You can stop in at a few boutiques before going to The Beach Road for dinner (be sure to make your reservations in advance). The restaurant offers a beautiful view of the water, nice ambience and great oysters. 

To top off the evening, we headed back to our inn and enjoyed drinks on the porch. There’s something about Martha’s Vineyard that helps you find a slower pace and appreciate a quiet porch evenings.  

Day 3: Edgartown and Chappaquiddick Island

Sights to See: Edgartown boutiques, Chappaquiddick Island, Cape Poge Wildlife Refuge, Cape Poge Lighthouse, classic beach bonfire 

Where to Eat: Biscuit (Oak Bluffs), Among the Flowers (Edgartown), Bangkok Cuisine (Oak Bluffs)
Drinks to Clink: BYOB on the beach 

To see more of Oak Bluffs, we started the morning with another walk along the harbor to East Chop Drive, giving us a great view of the town before heading to Biscuits for breakfast. 

We then hopped on the bus to Edgartown and bopped around downtown from boutique-to-boutique until it was time for lunch on the patio at Among the Flowers. 

Last minute, we booked a tour with Trustees to see Cape Poge Wildlife Refuge and Cape Poge Lighthouse, and this was one of our favorite experiences on the island. I can’t recommend this tour enough. The guide was fantastic and the scenery was beautiful. The area is completely off-the-grid and the tour allows you to climb to the top of the lighthouse. Our guide drove us on the beach, and we even saw a shipwreck they recently uncovered from the 1800s. 

After the tour, we headed back to Oak Bluffs to grab takeout from Bangkok and set off with our inn owners Erik and Rhonda for a sunset beach bonfire. 

With wine in hand, a cozy fire, pink sky and the beach to ourselves, it was an unexpected surprise that truly made our last night in Martha’s Vineyard unforgettable. 

Day 4: Gingerbread Houses & Departure Day 

Sights to See: Gingerbread Cottage Village 

Where to Eat: Lookout Tavern, Back Door Donuts

Drinks to Clink: Lookout Tavern 

Take my advice - take a later ferry if you can. It was nice to sleep in and take our time in the morning before getting back into travel mode. 

We enjoyed breakfast on the porch, indulging in another treat from Back Door Donuts and a homemade cobbler from the inn. 

Savoring our last morning in Martha’s Vineyard, we walked the neighborhood and worked our way to the colorful Gingerbread Cottage Village. These are some of the most adorable houses I’ve ever seen, and some of these fairytale cottages date back to the 1800s. 

After a late checkout, we were dropped off at Lookout Tavern for lunch. This spot is ideal before you take the ferry back since it sits right across the street. We opted for the lobster bisque and a lobster roll - which was the best one we had on the island. 

With good food and water views, it was the ideal sendoff to our mother-daughter weekend at Martha’s.

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