Joe’s cousin got married last weekend on Martha’s Vineyard, and we brought the family along for the ride. I have always wanted to visit, but had no real agenda other than to show up, eat lots of fresh seafood, and look around.

We went in early June, which is not high season. The hydrangeas everyone photographs weren’t out yet. What was in bloom were cascading azaleas and climbing roses in every color. 

What I didn’t expect was to be genuinely shaken by how beautiful some of these places are. The buildings are nearly 200 years old, and in some neighborhoods, there wasn’t a shabby salt-weathered chipped door in sight. They were so polished and white they gleamed. 

---

What to Know Before Visiting Martha’s Vineyard

Martha’s Vineyard is six towns in one island, and they are all very different. It’s smart to budget time to move between them because travel takes longer than you think, and traffic in peak season can make it genuinely annoying. We were here in early June, but The Taste of the Vineyard was happening, and we got only a taste of what traffic would be like in August. Bikes are your best friend. 

Edgartown

Edgartown is the one that almost broke me it was so beautiful. I kept stopping in the middle of the sidewalk to look at the buildings. The level of craftsmanship and the commitment to maintaining it is something I have never seen at that scale outside of a museum. White clapboard captains’ houses, immaculate gardens, brick sidewalks, zero visible neglect. The sidewalk was probably cleaner than my kitchen floor. It is historic architectural perfection, block after block. It’s almost surreal; it did haunt me a bit. This is what you probably are thinking of when you hear “Martha’s Vineyard.” Had the hydrangeas been in bloom, I’d have had a stroke, possibly. 

Oak Bluffs

Oak Bluffs is the counter-note to Edgartown’s restraint. Joyous and candy-colored, loud in the best way. It’s home to the famous gingerbread cottages in the most vibrant and exciting color combinations you could imagine. You’ll find 318 Victorian homes still standing in the old Methodist campground, painted in pinks and greens and yellows, trimmed with intricate carved woodwork that I looked up and found to be called “Carpenter’s Gothic.”

The layout was intriguing, and we found out the whole neighborhood started as a tent revival in 1835. Methodists came to camp and eventually built permanent structures meant to mimic the shape of their original tents. At its peak, there were 570 of them. Today, the ones that remain are a National Historic Landmark, and once a year in August, they hang paper lanterns outside and light them all at once. It’s called Illumination Night, and it’s been happening since 1869. I will be coming back for it.

We saw many homeowners out doing yardwork and maintenance on their properties, and you really got a sense of community here. It felt warm and inviting.

Chilmark

Chilmark is the one we didn’t make it to and still think about. Known for being quieter, more rural, and fiercely protected from overdevelopment… from what I gathered, it is the part of the island that people who really know the island love most. Next time.

Menemsha

Menemsha is a working fishing village on the western side of the island. Small, unassuming, exactly itself. There’s a fish market there that will ruin eating oysters anywhere else.

Aquinnah

Aquinnah is at the far western tip, where the Gay Head Lighthouse sits above the cliffs. Worth the drive.

Vineyard Haven

Vineyard Haven is where the ferry comes in, which we didn’t have time for. I hear it has good shopping and some beloved local spots.

Chappaquiddick Island

Chappaquiddick is a small island just off the eastern tip of Martha’s Vineyard. You can get there by a tiny two-car ferry that takes about two minutes. It’s mostly nature preserve and private land, very sparsely developed, known for being quiet and remote.

Some Practical Advice for Your Martha’s Vineyard Trip

Getting Here

You’re taking a ferry, most likely. There are some direct flights (we happened to book one from LGA with miles), but most people are taking a ferry. Our friends flew into Boston and rented a car to Woods Hole. From Woods Hole, it’s about 45 minutes to Vineyard Haven. Book ahead, especially if you’re bringing a car, as vehicle reservations sell out months in advance. Foot passengers have more flexibility.

Getting Around

You need a car for the western parts of the island, including Aquinnah and Menemsha. Within Edgartown and Oak Bluffs, you can walk or rent a bike.

When to Go

Early June was ideal for us. It was somewhat uncrowded (aside from the Taste of the Vineyard nights), warm enough, and the spring blooms were at their most intense. Peak season is July and August, when prices spike and the roads get legitimately difficult. If you can go in shoulder season, do it.

What to Wear

Whatever you packed is probably fine. The island skews casual in ways that make the formal elegance of Edgartown feel like an interesting contrast rather than a dress code. It’s definitely more relaxed than I had thought it would be. 

My Martha’s Vineyard Favorites

Morning Glory Farm (Edgartown)

Morning Glory Farm is an institution! Get there early for the baked goods. The corn muffins and cheddar biscuits are non-negotiable. We bought produce for dinner and ate pastries on the way to the car. The farm stand has a quality to it that makes you want to slow down.

Menemsha Fish Market

Go to the fish market, buy whatever they tell you is fresh, and sit on the beach. The village is tiny and operates like clockwork. There are some art galleries scattered about, and a very nice beach for swimming and shelling. Lobster rolls eaten outside, feet in the sand, BBQ chips. I was very happy here. 

Mad Martha’s Ice Cream(Edgartown, Oak Bluffs, Vineyard Haven)

Mad Martha’s was where people suggested we get ice cream, and it’s delicious. Always busy.

Jaws Bridge (Edgartown)

You can shell here. We did some people-watching—they were jumping off the bridge into the water below, which is a tradition that has nothing to do with the movie except proximity to the filming location. But the shelling is real, and the views are lovely. 

Gingerbread Cottages (Oak Bluffs)

Walk through them slowly. Don’t rush this. The Cottage Museum at the entrance is worth a few minutes to learn more about buildings. There’s a prototype cottage furnished as it would have looked in the 1880s. Then wander the pedestrian lanes and look at what people have done with color and detail on a very small scale.

More Martha’s Vineyard Recommendations

I polled some friends and our Instagram audience for their favorite Martha’s Vineyard stops. Here’s what they love and recommend. Save to Google Maps for easy reference on your trip!

Vacation Rentals

• Coldwell Banker/MV Landmarks
• Tea Lane Associates
• Sandpiper Rentals
• Martha’s Vineyard Vacation Rentals

Hotels

• Faraway (Edgartown)
• Winnetu (Edgartown)
• Harbor View Hotel (Edgartown)
• The Hob Knob Hotel (Edgartown)
• Beach Plum Inn (Menemsha)
• Mansion House Inn (Vineyard Haven)
• Summercamp Hotel (Oak Bluffs)
• Outermost Inn (Aquinnah)

Restaurants & Food

• Nomans (Oak Bluffs): Casual family dinner
• Chillmark General Store: Pizza
• State Road (West Tisbury): Dinner, open year-round
• Among the Flowers Café (Edgartown): Lunch, outdoor patio
• The Net Result (Vineyard Haven): Fried clams, steamed lobster, takeout
• The Sweet Life Cafe (Oak Bluffs): Special occasion dinner, garden patio
• Back Door Donuts (Oak Bluffs): Evenings only, opens at 7 p.m. but the line starts earlier
• Pie Chicks (Vineyard Haven): Pie
• The Newes from American (Edgartown): Elevated fare in a historic pub
• Seafood Shanty (Edgartown): Lunch on the deck
• Bad Martha Farmer’s Brewery (Edgartown): Beer and live music
• Donovan’s Reef (Oak Bluffs): Casual cocktail bar right on the harbor (try the Dirty Banana)
• Larsen’s Fish Market (Chilmark): Lobster rolls at sunset

Farms & Markets

• West Tisbury Farmers’ Market: Get the citrus cooler and salt rock chocolate
• Morning Glory Farm (Edgartown): Daily farm stand with farm-to-table goods
• Tea Lane Farm: Roadside flower stand with an honor system
• North Tabor Farm (Chilmark): Roadside farm stand with an honor system

Shopping

• Nochi (Vineyard Haven): Clothing
• Rags (Edgartown): Clothing
• CB Stark (Vineyard Haven, Edgartown): Jewelry and accessories
• Tracker Home Décor (Edgartown)
• Chappaquiddick Wood Company: Wooden bowls
• Up-Island Pottery (Chilmark)
• Marshall Farm Woodworks (Chappaquiddick): Stools
• Island Alpaca (Vineyard Haven): Baskets
• Vineyard Vines (Edgartown): Visit their very first storefront
• The Beach House (Vineyard Haven): Beautiful housewares, including a great linen collection
• Rainy Day (Vineyard Haven): Gift shop with all the essentials
• Granary Gallery (West Tisbury): Regional art

Nature & Activities

• Lambert’s Cove Beach (West Tisbury): Residents/renters only
• Long Point Beach (West Tisbury): Less crowded, adjacent swimming pond
• Felix Neck Wildlife Sanctuary (Edgartown): Hiking
• Cedar Tree Neck Sanctuary (Vineyard Haven): Hiking
• Lucy Vincent Beach (Chilmark): A coveted location, Beach Plum Inn has passes
• Menemsha Beach: Great place to watch the sunset
• East Chop Bluffs (Oak Bluffs): Lighthouse, scenic drive
• West Chop (Tisbury): Historic summer homes, great spot for an evening drive
• Aquinnah/Gay Head Cliffs: Visit the lighthouse and walk down to the beach
• Flying Horses Carousel: Perfect stop with kids
• Edgartown Cinema: Stop for a Jaws screening on a rainy day