photo by Marnely Murray

If you only have one day to explore Oak Bluffs, you’re in for a treat. This vibrant harbor town on Martha’s Vineyard blends seaside charm, colorful history, and an energetic, welcoming spirit that makes it one of the Island’s most beloved destinations. From coffee by the harbor to sunset strolls and late-night treats, Oak Bluffs offers the perfect mix of relaxation and adventure in just one day.

Whether you’re arriving by ferry for a quick visit or staying nearby, this guide will help you make the most of your 24 hours in Oak Bluffs.

Getting to Oak Bluffs

During the summer months, Oak Bluffs is one of the Island’s busiest ferry ports, welcoming visitors from across New England. Ferries from Seastreak Ferry, HyLine Cruises, The Island Queen, and the Rhode Island-Martha's Vineyard Fast Ferry all dock directly in the Oak Bluffs Harbor, making it a convenient and scenic arrival point.

The Steamship Authority Ferry, which operates year-round, also docks in Oak Bluffs during the peak season. In the off-season, the Steamship Authority runs exclusively to Vineyard Haven, about 15 minutes away. From there, it’s an easy ride on the Vineyard Transit Authority (VTA) Bus, which currently runs free of charge and connects visitors directly to Oak Bluffs.

Morning: Coffee, Views, and a Walk Through History

photo by Marnely Murray

Start your day early with a peaceful walk along the Oak Bluffs harbor. Watch as ferries pull in and fishing boats head out for the day. Stop by Aalia’s Coffee, a cozy and modern café that serves excellent espresso, breakfast pastries, and light bites, the perfect fuel for a day of exploring.

After breakfast, stroll through the Gingerbread Cottages in the Martha’s Vineyard Campground Meeting Association, affectionately known as the Campground. With their candy-colored trim and storybook charm, these Victorian cottages are some of the most photographed homes on the Island. Don’t miss the Tabernacle, an impressive open-air iron structure that has served as the community’s centerpiece for over a century.

It’s a peaceful and fascinating glimpse into the Island’s history, and one of the most scenic spots to start your day.

photo by Marnely Murray

Late Morning: Beaches and Bikes

After exploring the Campground, head toward Inkwell Beach, a short walk from downtown. This sandy stretch is ideal for a quick swim, a beach walk, or a few minutes of quiet relaxation.

To explore more of the coast, rent a bike from Vineyard Bike Rental Co., conveniently located near the ferry terminal. A scenic ride along Ocean Park offers sweeping ocean views and a look at some of the town’s grand Victorian homes. Continue down the path toward Joseph Sylvia State Beach, which connects Oak Bluffs and Edgartown.

This beach is home to the famous “Jaws Bridge,” where locals and visitors alike have jumped into the clear waters for generations. Whether you take the leap or just snap a photo, it’s a classic Oak Bluffs experience that captures the fun, carefree spirit of the Island.

Lunch: Fresh Flavors and Local Favorites

By midday, Oak Bluffs’ dining scene comes alive with options for every taste.

Mo’s Lunch is a local favorite for fresh, creative sandwiches, soups, and daily specials, plus baked goods by Korilee the baker; her cookies and cakes are Island-famous. Tigerhawk Sandwich Co. is another excellent option for thoughtful, flavorful sandwiches made with locally sourced ingredients and house-baked bread.

If you want to enjoy lunch by the water, Lookout Tavern offers panoramic ocean views and a menu filled with sushi, lobster rolls, and casual coastal fare. For vibrant, modern Mexican food, head to Dos Mas for flavorful tacos, burritos, and margaritas that pair perfectly with the beachy atmosphere.

MV Salads serves fresh, creative salads made with local produce, perfect for a lighter option on a warm day. And if you’re looking for a lively waterfront scene, Sandbar & Grille is a relaxed open-air spot right on the harbor, ideal for a mid-afternoon cocktail and a bite to eat.

Afternoon: Shopping, Sweets, and Classic Fun

After lunch, take a stroll through downtown Oak Bluffs, where Circuit Avenue buzzes with boutiques, galleries, and shops filled with Island-made treasures.

Start with Stefanie Wolf Designs, where colorful glass bead jewelry is handcrafted right in the studio. Sanctuary offers a peaceful shopping experience with curated gifts, books, and home goods, while Third World Trading Co. showcases globally inspired clothing and accessories that reflect the creative, eclectic spirit of the town.

Stop into Craftworks for unique, locally made pottery, glass, and art. Each piece feels distinctly Vineyard and makes for a beautiful keepsake.

For a dose of nostalgic fun, don’t miss the Ryan Family Amusements on Circuit Avenue. Whether you’re traveling with kids or simply want to relive a bit of childhood, this classic arcade is packed with games, from skee-ball to air hockey to claw machines.

Back Door Donuts, photo by Marnely Murray

And of course, you can’t spend an afternoon in Oak Bluffs without indulging your sweet tooth. Back Door Donuts is an Island institution, famous for its warm apple fritters and late-night treats. During the day, pop by Bill’s Chocolate Emporium for homemade fudge or their iconic lobster ice cream. The Good Shoppe is another delightful stop, offering playful gifts, small-batch sweets, and local charm in every corner.

Evening: Dinner, Drinks, and a Vineyard Sunset

As the sun begins to dip, Oak Bluffs takes on a magical glow. The harbor lights shimmer across the water, and the town fills with the hum of evening diners and live music.

For dinner, Offshore Ale Co. is a local favorite. This cozy brewpub serves wood-fired pizzas, Island-made craft beers, and hearty New England dishes in a rustic, welcoming setting.

Sweet Life Café, another dinner option, tucked into a charming Victorian house on Circuit Avenue, offers seasonal New American fare with French flair, a thoughtful wine list, and inventive cocktails, all served in a relaxed, candlelit garden patio or cozy dining rooms.

If you’re looking for something a bit more upscale, Red Cat Kitchen offers a refined yet relaxed dining experience, featuring farm-to-table dishes made with local seafood and Island-grown produce.

Sandbar & Grille is perfect for those who want to dine right by the beach with their toes in the sand, while Lookout Tavern remains a top choice for casual waterfront dining with unbeatable views.

After dinner, take a peaceful walk through Ocean Park, where you can sit on the grass and watch the ferries light up the night sky. In summer, you might even catch a concert or fireworks display, an unforgettable way to end your 24 hours in Oak Bluffs.

Where to Stay in Oak Bluffs

photo by Marnely Murray

If you’re spending the night, Oak Bluffs offers plenty of charming places to stay. Summercamp Hotel, with its bright nautical décor and prime harbor views, captures the playful energy of the town. The Oak Bluffs Inn offers an intimate boutique experience in the heart of downtown, while The Attleboro House provides historic charm and unbeatable proximity to the harbor.

A Perfect Vineyard Day

Spending 24 hours in Oak Bluffs is the perfect introduction to the magic of Martha’s Vineyard. This colorful town has it all: rich history, incredible food, unique shopping, and a relaxed coastal atmosphere that invites you to slow down and enjoy the moment.

From your first coffee at Aalia’s to your last bite at Back Door Donuts, Oak Bluffs captures the essence of Island life in every detail. Whether you come for a day or stay for a week, it’s a place that will have you planning your return before you even leave the harbor.