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The place to Eat, Discover, Keep

Admin by Admin
August 26, 2026
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The place to Eat, Discover, Keep
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Martha's Vineyard downtown restaurant with outdoor seating and a striped awning

Joe’s cousin received married final weekend on Martha’s Winery, and we introduced the household alongside for the trip. I’ve at all times wished to go to, however had no actual agenda apart from to point out up, eat plenty of recent seafood, and go searching.

We went in early June, which isn’t excessive season. The hydrangeas everybody pictures weren’t out but. What was in bloom had been cascading azaleas and climbing roses in each shade. 

What I didn’t count on was to be genuinely shaken by how lovely a few of these locations are. The buildings are almost 200 years outdated, and in some neighborhoods, there wasn’t a shabby salt-weathered chipped door in sight. They had been so polished and white they gleamed. 

white house with shutters and a white picket fence in edgartown martha's vineyard

What to Know Earlier than Visiting Martha’s Winery

Martha’s Winery is six cities in a single island, and they’re all very totally different. It’s sensible to price range time to maneuver between them as a result of journey takes longer than you assume, and visitors in peak season could make it genuinely annoying. We had been right here in early June, however The Style of the Winery was occurring, and we received solely a style of what visitors could be like in August. Bikes are your finest buddy. 

Edgartown

Edgartown is the one that nearly broke me it was so lovely. I stored stopping in the course of the sidewalk to have a look at the buildings. The extent of workmanship and the dedication to sustaining it’s one thing I’ve by no means seen at that scale exterior of a museum. White clapboard captains’ homes, immaculate gardens, brick sidewalks, zero seen neglect. The sidewalk was most likely cleaner than my kitchen ground. It’s historic architectural perfection, block after block. It’s nearly surreal; it did hang-out me a bit. That is what you most likely are considering of if you hear “Martha’s Winery.” Had the hydrangeas been in bloom, I’d have had a stroke, presumably. 

Cedar shingled house with white picket fence and brick chimneys in martha's vineyard

Oak Bluffs

Oak Bluffs is the counter-note to Edgartown’s restraint. Joyous and candy-colored, loud in one of the best ways. It’s dwelling to the well-known gingerbread cottages in essentially the most vibrant and thrilling shade mixtures you could possibly think about. You’ll discover 318 Victorian houses nonetheless standing within the outdated Methodist campground, painted in pinks and greens and yellows, trimmed with intricate carved woodwork that I regarded up and located to be referred to as “Carpenter’s Gothic.”

The structure was intriguing, and we discovered the entire neighborhood began as a tent revival in 1835. Methodists got here to camp and ultimately constructed everlasting buildings meant to imitate the form of their authentic tents. At its peak, there have been 570 of them. At this time, those that stay are a Nationwide Historic Landmark, and yearly in August, they grasp paper lanterns exterior and lightweight them abruptly. It’s referred to as Illumination Evening, and it’s been occurring since 1869. I shall be coming again for it.

We noticed many owners out doing yardwork and upkeep on their properties, and you actually received a way of neighborhood right here. It felt heat and welcoming.

posing in front of a gingerbread cottage in martha's vineyard
purple gingerbread cottage in oak bluffs
salmon pink gingerbread cottage in Martha's Vineyard

Chilmark

Chilmark is the one we didn’t make it to and nonetheless take into consideration. Recognized for being quieter, extra rural, and fiercely protected against overdevelopment… from what I gathered, it’s the a part of the island that individuals who actually know the island love most. Subsequent time.

Menemsha

Menemsha is a working fishing village on the western facet of the island. Small, unassuming, precisely itself. There’s a fish market there that may smash consuming oysters anyplace else.

Aquinnah

Aquinnah is on the far western tip, the place the Homosexual Head Lighthouse sits above the cliffs. Well worth the drive.

posing on top of gay head lighthouse in martha's vineyard

Winery Haven

Winery Haven is the place the ferry is available in, which we didn’t have time for. I hear it has good buying and a few beloved native spots.

Chappaquiddick Island

Chappaquiddick is a small island simply off the japanese tip of Martha’s Winery. You will get there by a tiny two-car ferry that takes about two minutes. It’s principally nature protect and personal land, very sparsely developed, recognized for being quiet and distant.

Martha's Vineyard Edgartown Street with eggshell blue car and brick sidewalks

Some Sensible Recommendation for Your Martha’s Winery Journey

Getting Right here

You’re taking a ferry, almost certainly. There are some direct flights (we occurred to ebook one from LGA with miles), however most individuals are taking a ferry. Our buddies flew into Boston and rented a automobile to Woods Gap. From Woods Gap, it’s about 45 minutes to Winery Haven. Guide forward, particularly when you’re bringing a automobile, as automobile reservations promote out months upfront. Foot passengers have extra flexibility.

Nantucket Airlines Plane Martha's Vineyard

Getting Round

You want a automobile for the western components of the island, together with Aquinnah and Menemsha. Inside Edgartown and Oak Bluffs, you’ll be able to stroll or hire a motorbike.

When to Go

Early June was superb for us. It was considerably uncrowded (except for the Style of the Winery nights), heat sufficient, and the spring blooms had been at their most intense. Peak season is July and August, when costs spike and the roads get legitimately troublesome. For those who can go in shoulder season, do it.

What to Put on

No matter you packed might be high-quality. The island skews informal in ways in which make the formal class of Edgartown really feel like an fascinating distinction quite than a gown code. It’s positively extra relaxed than I had thought it could be. 

Martha's Vineyard House with blue shutters
Kate Arends Martha's Vineyard Travel Guide

My Martha’s Winery Favorites

Morning Glory Farm (Edgartown)

Morning Glory Farm is an establishment! Get there early for the baked items. The corn muffins and cheddar biscuits are non-negotiable. We purchased produce for dinner and ate pastries on the best way to the automobile. The farm stand has a high quality to it that makes you wish to decelerate.

Menemsha Fish Market

Go to the fish market, purchase no matter they inform you is recent, and sit on the seaside. The village is tiny and operates like clockwork. There are some artwork galleries scattered about, and a really good seaside for swimming and shelling. Lobster rolls eaten exterior, toes within the sand, BBQ chips. I used to be very blissful right here. 

Menemsha Fish Market sign Martha's Vineyard
Martha's Vineyard woman eating a Lobster Roll on a bench outside

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

Mad Martha’s was the place folks steered we get ice cream, and it’s scrumptious. All the time busy.

Jaws Bridge (Edgartown)

You’ll be able to shell right here. We did some people-watching—they had been leaping off the bridge into the water beneath, which is a practice that has nothing to do with the film besides proximity to the filming location. However the shelling is actual, and the views are pretty. 

posing on top of the jaws bridge in martha's vineyard

Gingerbread Cottages (Oak Bluffs)

Stroll via them slowly. Don’t rush this. The Cottage Museum on the entrance is value a couple of minutes to study extra about buildings. There’s a prototype cottage furnished as it could have regarded within the Eighties. Then wander the pedestrian lanes and have a look at what folks have finished with shade and element on a really small scale.

ywllo fun size gingerbread cottage in martha's vineyard

Extra Martha’s Winery Suggestions

I polled some buddies and our Instagram viewers for his or her favourite Martha’s Winery stops. Right here’s what they love and suggest. Save to Google Maps for simple reference in your journey!

Trip Leases

Lodges

date date in martha's vineyard at a restaurant next to the water

Eating places & Meals

martha's vineyard lobster roll in a to-go box
larsen's fish market sign in martha's vineyard

Farms & Markets

Buying

beware sharks sign on the side of a building in martha's vineyard
Martha's Vineyard Edgartown League of Gentleman sign

Nature & Actions

  • Lambert’s Cove Seashore (West Tisbury): Residents/renters solely
  • Lengthy Level Seashore (West Tisbury): Much less crowded, adjoining swimming pond
  • Felix Neck Wildlife Sanctuary (Edgartown): Climbing
  • Cedar Tree Neck Sanctuary (Winery Haven): Climbing
  • Lucy Vincent Seashore (Chilmark): A coveted location, Seashore Plum Inn has passes
  • Menemsha Seashore: Excellent spot to look at the sundown
  • East Chop Bluffs (Oak Bluffs): Lighthouse, scenic drive
  • West Chop (Tisbury): Historic summer time houses, good spot for a night drive
  • Aquinnah/Homosexual Head Cliffs: Go to the lighthouse and stroll right down to the seaside
  • Flying Horses Carousel: Excellent cease with youngsters
  • Edgartown Cinema: Cease for a Jaws screening on a wet day
a person walking on a marths's vineyard beach

Kate is the founding father of Wit & Delight. She is presently studying find out how to play tennis and is ceaselessly testing the boundaries of her inventive muscle. Comply with her on Instagram at @witanddelight_.



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The place to Eat, Discover, Keep

The place to Eat, Discover, Keep

August 26, 2026
The Spook College Reunite For New Album ‘Like A Heartbeat’: Hear “Falling”

The Spook College Reunite For New Album ‘Like A Heartbeat’: Hear “Falling”

August 26, 2026
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