How to Spend the Perfect Day in Oak Bluffs

Oak Bluffs is a vibrant and popular destination on Martha’s Vineyard, attracting a steady stream of visitors throughout the year, especially when the Steamship Authority resumes its seasonal ferry route to the town each May. As one of the primary gateways to the Island, Oak Bluffs welcomes numerous travelers who come by ferry to explore its lively streets and scenic surroundings. This charming and walkable town is a favorite among tourists, offering a plethora of activities that make it ideal for both day trips and longer stays. With beautiful beaches, diverse dining options, unique shopping experiences, picturesque parks, rich history, and a bustling harbor, Oak Bluffs has something for everyone. Our How To Spend The Perfect Day In Oak Bluffs guide will help you make the most of your day in Oak Bluffs, ensuring you experience the best the town has to offer.

How to Spend the Perfect Day in Oak Bluffs Oak Bluffs Harbor
A view from Oak Bluffs Harbor.

Oak Bluffs boasts a rich history that began in 1835 when Jeremiah Pease selected the area for a Methodist camp meeting. This popular religious gathering led to the establishment of the Martha’s Vineyard Campmeeting Association, where tents were eventually replaced by ornate cottages, earning the area the nickname “Cottage City” when it separated from Edgartown in 1880. Renamed Oak Bluffs in 1907, the town is home to the historic Flying Horses Carousel, brought from Coney Island in 1884 and the oldest platform carousel still in operation in the U.S. Today, the Camp Meeting Association grounds and the carousel are designated National Historic Landmarks, preserving Oak Bluffs’ unique heritage.

How to Spend the Perfect Day in Oak Bluffs – Visit the Gingerbread Cottages

How to Spend the Perfect Day in Oak Bluffs Visit the Gingerbread Cottages in the Campground
The iconic gingerbread cottages of the Martha’s Vineyard Camp Meeting Association.

To start off your day in Oak Bluffs, grab a coffee from one of the local favorites like Mocha Motts or Aalia’s. With your coffee in hand, head to the Campgrounds, where you’ll find the charming Gingerbread Cottages, which originally began as the Methodist gathering spot mentioned above. Take a leisurely stroll through this historic area and enjoy the bright, colorful houses adorned with intricate details. It’s the perfect way to soak in the unique architecture and vibrant atmosphere while experiencing a little history! Save the date for the third Wednesday in August each year when the gingerbread cottages light up in unison during the Grand Illumination event, the crown jewel of the Campground season! 

How to Spend the Perfect Day in Oak Bluffs – Explore the Beaches

How to Spend the Perfect Day in Oak Bluffs Explore Beaches
The beaches of Oak Bluffs are open to the public and within walking distance from the ferry.

Oak Bluffs boasts beautiful beaches perfect for a day of relaxation and fun. Just a few minutes from town, near where the Steamship Authority docks, you’ll find public beaches on both sides of the dock. For those feeling a bit more adventurous, consider renting bikes from All Star Bike Rentals and taking a scenic 1.5-mile ride to Joseph Sylvia State Beach. This picturesque bike path offers stunning views, with the ocean on one side and a coastal pond on the other, making it an ideal spot for both biking and enjoying the natural beauty of Martha’s Vineyard.

How to Spend the Perfect Day in Oak Bluffs – Enjoy Lunch on the Harbor

Oak Bluffs harbor is bustling with activity in the summer months.

After meandering through the cottages and admiring the beaches, you’ll likely be ready for lunch. We recommend dining along the harbor to enjoy the scenic water, boat views, and of course, the entertainment of people watching. As you stroll along the harbor, you’ll find a variety of restaurants, each offering a casual and fun vibe with delicious seafood options. Nancy’s is a popular choice, featuring a downstairs deck where you can walk up and order bar-style food, and an upstairs dining room and patio with a more extensive restaurant menu overlooking the harbor. Coop de Ville is another favorite  known for its wings, seafood specials, and extensive beer selection. Whether you’re in the mood for a quick bite or a leisurely meal, the harbor area has something to satisfy every palate.

How to Spend the Perfect Day in Oak Bluffs – Shop Around Town

Circuit Avenue is a popular shopping destination in Oak Bluffs.

After lunch, it’s time to explore the local shops. Circuit Avenue is the main street of Oak Bluffs and the perfect place to start. Here, you’ll find a variety of stores. If you’re looking for boutique clothing stores, take a look at Basics and Eastway, Island Outfitters, and Slip 77. There are also souvenir shops, jewelry stores, and local art galleries. Don’t forget to venture off Circuit Avenue as well, where you’ll discover even more unique shops. Take your time wandering around and picking up a special memento from your trip to remember your day in Oak Bluffs.

How to Spend the Perfect Day in Oak Bluffs – Ride the Flying Horses Carousel

The Flying Horses Carousel is the nation’s oldest platform carousel. Photo credit Vineyard Preservation Trust.

No visit to Oak Bluffs is complete without a ride on the Flying Horses Carousel. This historic carousel, built in 1876 and the oldest platform carousel in the United States, offers a nostalgic and fun experience for all ages. As you ride, try to catch the brass ring for an extra touch of excitement. Located just a few blocks inland from the ocean, the Flying Horses Carousel is a delightful blend of history and entertainment, making it a must-visit attraction during your day in Oak Bluffs.

How to Spend the Perfect Day in Oak Bluffs – Soak Up Ocean Park

Ocean Park is a picture-perfect destination and a relaxing place to unwind.

Ocean Park is a picturesque retreat on Martha’s Vineyard where lush green spaces meet the sparkling Atlantic. Stroll along the charming walkways, relax by the iconic gazebo, and take in the breathtaking views of the ocean. It’s the perfect place to unwind, have a picnic, fly a kite, read a book or just sit and enjoy the view. Look out for summer concerts and special events that bring this historic park to life with music and community spirit.

How to Spend the Perfect Day in Oak Bluffs – Wine and Dine in Cottage City

Circuit Avenue, nearby Kennebec Avenue, and Oak Bluffs harbor offer many dining options.

When it comes to dinner options in Oak Bluffs, the choices are abundant and diverse. For a refined dining experience, look no further than The Sweet Life, where locally sourced ingredients from fishermen and farmers shine in their dishes. With both indoor and outdoor seating, including a beautifully lit patio, The Sweet Life offers a semi-formal ambiance perfect for a special evening out. For a lively atmosphere and unique menu, head to Red Cat Kitchen, located right on Circuit Avenue. This vibrant dining spot promises a fun and memorable dining experience. Meanwhile, The Pawnee House, run by a husband and wife team, offers a quaint dining room and a menu that caters to both meat-eaters and vegans alike. If you’re willing to venture a bit outside of downtown, consider heading to Nomans, just a mile away, for a large outdoor dining venue complete with a spacious lawn, games, and live music during the summer months, plus its dog-friendly and they offer a courtesy shuttle from the Steamship Authority. This is just a start to some of the amazing dining options to discover in this town. With such an array of dining options, Oak Bluffs ensures that every palate is satisfied. If you’re up for a nightcap, Oak Bluffs is also a popular nightlife destination.

Oak Bluffs: Save Room for Dessert

Mad Martha’s ice cream is a favorite spot for sweet treats.

Before you head back on the boat or retire to your vacation rental, treat yourself to some dessert in Oak Bluffs. Indulge in an iconic Martha’s Vineyard staple at Back Door Donuts, where the daytime bakery transforms into a late-night delight, serving up fresh, warm donuts from its back door in the parking lot. While the line may be long, the experience is well worth it. Alternatively, satisfy your sweet tooth at one of the many ice cream shops conveniently located right on Circuit Avenue, including favorites like Mad Martha’s and Ben & Bill’s Chocolate Emporium. Whether you opt for piping hot donuts or creamy scoops of ice cream, ending your day with a delectable treat is the perfect way to complete your Oak Bluffs adventure.

As your day in Oak Bluffs winds down, we hope you’ve discovered the charm and excitement this vibrant town has to offer. From its historic landmarks to its bustling harbor and delicious dining options, Oak Bluffs provides a memorable taste of Martha’s Vineyard life. We hope the experiences and adventures you’ve had here inspire you to return and explore the unique offerings of the Island’s other towns. Martha’s Vineyard promises countless more treasures to uncover on your next visit!

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