Oak Bluffs, Massachusetts, is a vibrant town located on Martha’s Vineyard. Known for its colorful “gingerbread” cottages and lively community, Oak Bluffs has a rich history as a summer resort destination. The town grew from a Methodist camp meeting ground into a bustling hub of activity and culture. Oak Bluffs’ welcoming atmosphere and strong community ties make it a special place to experience the charm of Martha’s Vineyard. Its blend of historical significance and modern vibrancy creates an unforgettable destination.
Looking for what to do here? Check out the best and fun things to do when you visit.
Things To Do In Oak Bluffs, MA
1. Stroll through the charming Oak Bluffs Campground
Oak Bluffs Campground
The Oak Bluffs Campground is a unique historical site filled with charm. This area features picturesque gingerbread cottages, each painted in bright colors. The cottages provide a glimpse into the summer colony lifestyle from the late 19th century.
While walking, look at the intricate designs and vibrant hues of each home. Some cottages are over 100 years old. The atmosphere is peaceful, making it a wonderful place for leisurely strolls or taking pictures.
During summer, the campground hosts various events and gatherings. Families often sit on porches, enjoying quality time together. The community vibe is infectious, attracting visitors from near and far.
Be sure to visit the Tabernacle, an open-air church with stunning architecture. It’s a fantastic spot to enjoy concerts and community events during the summer. Whether you are a history buff or just love colorful places, this location is a must-see.
Overall, a stroll through the Oak Bluffs Campground captures the essence of Martha’s Vineyard. You’ll leave feeling relaxed and inspired.
Address: 1 Trinity Park, Oak Bluffs, MA 02557.
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2. Relax on the beautiful Oak Bluffs Beach
Oak Bluffs Beach is the perfect destination for sun lovers and beachgoers. Nestled along the shore, this beach offers soft sand and gentle waves. People of all ages flock to this beautiful spot for sunbathing, swimming, and sandcastle building.
The beach is well-maintained and provides various amenities. You’ll find restrooms, showers, and lifeguards on duty during peak hours. These features create a safe environment for families and visitors.
Nearby, there are picnic areas where you can enjoy a meal while soaking in the ocean view. Many love to grab a bite from local eateries close to the beach. You can also rent equipment for water sports like paddleboarding or kayaking.
In the evening, the golden sun setting over the water creates a magical atmosphere. It’s the perfect backdrop for a romantic stroll or family gatherings. Oak Bluffs Beach is a place to unwind and enjoy the natural beauty of Martha’s Vineyard.
Address: 0 Sea View Ave, Oak Bluffs, MA 02557.
3. Visit the iconic Flying Horses Carousel
The Flying Horses Carousel is an enchanting experience for the whole family. It’s one of the oldest working carousels in the United States, dating back to 1876. The beautifully hand-painted horses and lively music bring a sense of nostalgia.
Riding the carousel is an exhilarating experience, especially for children. Each horse has unique artistic designs, making it a perfect spot for eager young riders. Grab the brass ring for a chance to win a free ride!
The carousel is not just a ride; it’s a piece of history. The craftsmanship involved in its creation is impressive. After riding, visitors are encouraged to explore the surrounding area, filled with quaint shops and snacks.
Make sure to capture photos to remember this magical moment. The carousel’s charm represents childhood memories and happiness. A visit to the Flying Horses Carousel promises joy and fun for every guest.
Address: 15 Oak Bluffs Ave, Oak Bluffs, MA 02557.
4. Explore the Martha’s Vineyard Museum
The Martha’s Vineyard Museum offers a deep dive into the rich history of the island. Housed in a beautiful building, the museum has engaging exhibits showcasing the area’s heritage. From whaling and sailing to local art, there is much to discover.
Visitors can explore artifacts, photographs, and documents that highlight the island’s past. This museum is especially interesting for history buffs wanting to learn more about Martha’s Vineyard and its residents.
Participate in guided tours led by knowledgeable staff. They provide insight into the exhibitions and tell fascinating stories about the island. The museum often hosts special events, conversations, and art exhibits throughout the year.
After exploring, take some time to relish the beautiful gardens on the premises. They provide a tranquil spot to reflect on your visit. Overall, the Martha’s Vineyard Museum is a wonderful place to explore and appreciate the island’s unique culture.
Address: 151 Lagoon Pond Rd, Vineyard Haven, MA 02568.
5. Enjoy a meal at a local seafood restaurant
No visit to Oak Bluffs is complete without savoring delicious seafood. The town boasts an array of seafood restaurants that cater to every palate. From casual eateries to upscale dining, you can find plenty of options.
Indulge in the island’s famous dishes, such as clam chowder, lobster rolls, or fresh-fried fish. Many restaurants source their ingredients locally, ensuring freshness and flavor. You’ll surely enjoy the unique blends of flavors found in Martha’s Vineyard’s cuisine.
Consider dining with a view at waterfront restaurants. Watching the sunset while enjoying seafood creates a magical dining experience. Some places even host live entertainment for added enjoyment.
Don’t forget to try the local specialties, often highlighted on seasonal menus. Optionally, many seafood spots offer takeout, allowing you to enjoy your meal on the beach. Eating out in Oak Bluffs promises delightful flavors and vibrant atmospheres.
Address: Varies by restaurant choice.
6. Take a bike ride around the scenic paths
Exploring Oak Bluffs by bike is an enjoyable way to soak in the beautiful scenery. Many bike rental shops offer a variety of options, from standard bicycles to tandem bikes. Riding along the coastal paths brings a fresh breeze and picturesque views.
There are several bicycle-friendly routes throughout Oak Bluffs and neighboring towns. One recommended trail leads you to scenic beaches and parks, allowing for stops along the way. Look for designated bike paths to ensure your safety.
Biking is great for the environment and allows you to cover more ground than walking. It’s an excellent way to reach attractions like beaches, businesses, and nature reserves. You may come across charming shops and local art along the way.
Take your time, enjoy the ride, and capture the sights and sounds of the island. Remember to wear a helmet and stay hydrated. Exploring Oak Bluffs by bike makes for an unforgettable adventure.
Address: Rental shops are located throughout Oak Bluffs.
7. Discover the colorful Gingerbread Cottages
The Gingerbread Cottages in Oak Bluffs are a delightful sight. These vibrant, intricately decorated houses date back to the 19th century. Their whimsical architecture and bright colors create a lively atmosphere in the neighborhood.
The area was initially built for Methodist summer meetings and has evolved into a charming community. Each cottage reflects unique designs, making each one special. Visitors often appreciate the craftsmanship and creativity involved in these residences.
Walking tours are popular, where you can learn about the history and significance of each cottage. Some have been passed down through generations, adding to their appeal. Photographers love capturing the beauty of these iconic structures.
During your visit, don’t hesitate to ask locals about the stories behind their homes. You might discover fascinating tales that add depth to your visit. Exploring the Gingerbread Cottages offers a peek into the island’s vibrant history.
Address: Campground, Oak Bluffs, MA 02557.
8. Visit the Oak Bluffs Harbor and Marina
The Oak Bluffs Harbor is a vibrant and picturesque area to explore. It’s a hub for boats and ferries, making it easy for visitors to navigate Martha’s Vineyard. The harbor offers stunning views of the water and surrounding landscape.
Stroll along the harbor while watching boats come and go. Fishermen, sailboats, and yachts create a lively scene. There are numerous spots to sit, relax, and enjoy the surround scenery. Local shops and cafés line the harbor, perfect for fresh seafood or a refreshing drink.
In the summer, the marina is bustling with activity. Seasonal events and local festivals are often held here. You can also hop onto a ferry to explore other parts of Martha’s Vineyard or take a scenic cruise.
For those interested in fishing, the harbor offers charters for deep-sea fishing or sailing excursions. A visit to the Oak Bluffs Harbor is an exciting way to connect with the heart of this coastal community.
Address: Oak Bluffs Harbor, Oak Bluffs, MA 02557.
9. Attend local art shows and community events
Oak Bluffs is known for its vibrant arts scene and community events. Throughout the year, locals and visitors can enjoy art shows featuring works from talented artists. The exhibits often showcase everything from paintings to sculpture and photography.
Check out local galleries and community spaces that host regular events. These gatherings provide an opportunity to connect with artists and learn about their inspirations. Celebrate creativity while enjoying refreshments and live music.
Community events such as farmers’ markets, cultural festivals, and concerts provide entertainment for all ages. These happenings are key to the town’s charm, fostering unity and supporting local businesses.
Don’t forget to look for announcements regarding seasonal activities throughout the year. Engaging with the local culture is an enriching experience that enhances your visit to Oak Bluffs. Embrace the arts and community spirit that the town offers!
Address: Various venues throughout Oak Bluffs.
10. Go fishing off the docks or charters
Fishing in Oak Bluffs is a popular activity for both residents and tourists. The area offers numerous docks and piers where you can cast your line without needing a boat. Visitors often enjoy catching species such as striped bass, bluefish, and more.
For those wanting a more extensive experience, consider a fishing charter. Professional guides will take you out to deeper waters, increasing the chance of landing trophy fish. These charters cater to all skill levels, ensuring a fun day on the water.
Before heading out, make sure you have the proper fishing license. Local shops provide gear rentals and supplies for your convenience. Fishing can be an exciting way to explore the coastline while enjoying nature.
Whether you’re casting from the dock or out at sea, Oak Bluffs provides a great backdrop for a fishing adventure. Don’t forget to bring your camera to capture the ocean’s beauty and any catches you make!
Address: Various docks in Oak Bluffs.
11. Enjoy a sunset cruise around the island
A sunset cruise around Martha’s Vineyard is an unforgettable experience. As the sun sets, the sky lights up with brilliant colors, creating a stunning backdrop for your boat ride. Various local companies offer cruises that leave from Oak Bluffs Harbor.
These cruises typically last a few hours and provide views of iconic landmarks, lighthouses, and coastal scenery. On board, guests can enjoy refreshments while relaxing with friends or family. It’s a great way to unwind after a day of exploring.
Some cruises even feature live music or have knowledgeable guides who share interesting facts about the area. The gentle sway of the boat and the sound of the waves create a peaceful atmosphere.
Whether you’re celebrating a special occasion or just looking to relax, a sunset cruise is a magical highlight of any visit to Oak Bluffs. Be sure to bring your camera to capture those beautiful moments on the water!
Address: Oak Bluffs Harbor, Oak Bluffs, MA 02557.
12. Visit the Tabernacle for summer concerts
The Tabernacle in Oak Bluffs is a historic outdoor venue that hosts summer concerts and events. This stunning structure features beautiful architecture and offers an enchanting ambiance. During the summer months, residents and visitors flock to the Tabernacle for lively performances.
Concerts range from classical and jazz to contemporary music and local artists. The acoustics in the Tabernacle provide delightful sound, enhancing your concert experience. Attending a show here is always a treat, as the atmosphere is filled with energy and excitement.
Grab a spot on the lawn or bring a blanket for a more laid-back experience. Many people enjoy picnicking while listening to fantastic music. The Tabernacle not only showcases great talent but also serves as a cultural centerpiece for the Oak Bluffs community.
Check the event schedule ahead of time so you won’t miss out on a performance. A night at the Tabernacle promises an unforgettable evening filled with music and good vibes.
Address: 25 Trinity Park, Oak Bluffs, MA 02557.
13. Explore the nearby nature trails at Manuel F. Correllus State Forest
Manuel F. Correllus State Forest is a beautiful escape for nature lovers. This protected area features well-marked trails that wind through diverse habitats. Whether you want to hike, walk, or bike, the forest offers plenty of recreational opportunities.
The area is rich in flora and fauna, making each visit unique. Birdwatchers will love the chance to spot various species, from songbirds to more elusive types. Walking along the trails allows you to immerse yourself in the sounds and sights of nature.
Many trails are relatively flat, making them accessible for a wide range of abilities. The scenery varies from dense woods to open spaces, offering beautiful views. Plan a picnic near one of the designated areas to fully enjoy your time in nature.
Correllus State Forest is a hidden gem near Oak Bluffs that provides perfect outdoor experiences. It’s an excellent place to take a break from the beach and enjoy the stunning landscapes of Martha’s Vineyard.
Address: 94 State Forest Rd, Vineyard Haven, MA 02568.
14. Take a ferry ride between Vineyard Haven and Oak Bluffs
Taking a ferry ride between Vineyard Haven and Oak Bluffs is a delightful way to travel and enjoy stunning views of the water. Ferries run regularly, providing a scenic and convenient way to hop between these charming towns on Martha’s Vineyard.
As you board, take a seat on the deck for an unobstructed view of the harbor and coastline. The short ride grants you glimpses of boats and wildlife, making it an enjoyable experience.
Ferry schedules are posted online, offering options to fit your travel plans. Be sure to arrive early, especially during busy summer months, to secure your spot and experience the hustle and bustle of the port.
The ride adds convenience to your island exploration and creates lasting memories of the beautiful waters surrounding Martha’s Vineyard. Experience the charm of island travel by ferry during your visit.
Address: Ferry Terminal, Oak Bluffs, MA 02557.
15. Try your luck at Ospreys Golf Course
Ospreys Golf Course offers a refreshing round of golf amidst stunning landscapes. This 18-hole course is open to players of all skill levels. The beautiful setting, combining rolling hills and lush greenery, creates an enjoyable playing experience.
Before teeing off, visitors can take advantage of the practice range to warm up. Whether you’re a seasoned player or a beginner, this course has something for everyone. The friendly staff are available to assist and provide guidance.
Throughout the course, you’ll encounter natural scenery that showcases the beauty of Martha’s Vineyard. It’s a great way to enjoy the outdoors while participating in a favorite pastime. After your game, relax with refreshments at the clubhouse.
For golf enthusiasts, Ospreys Golf Course completes a visit to Oak Bluffs with a perfect day on the greens. Don’t forget to book your tee time ahead during peak seasons!
Address: 90 South St, Oak Bluffs, MA 02557.
16. Join a guided tour of the island
Joining a guided tour of Martha’s Vineyard is a fantastic way to learn about the island’s rich history and hidden gems. Various tour companies offer different types of excursions, whether by bus, bike, or walking tours. Expert guides provide valuable insight into the local culture, architecture, and history.
Popular stops typically include charming towns, beautiful beaches, and scenic viewpoints. Each tour offers a unique perspective, showcasing different aspects of Martha’s Vineyard. Some tours even include food tastings or visits to notable landmarks.
Taking a guided tour allows you to sit back, relax, and absorb the island’s charm without the hassle of navigating. You’ll also meet fellow travelers, enhancing your experience.
Consider booking your tour in advance, especially during summer, to secure your spot. A guided tour is a fun way to connect with Martha’s Vineyard and gain appreciation for this beautiful island.
Address: Various starting points depending on the tour company.
17. Attend the Oak Bluffs Farmer’s Market
The Oak Bluffs Farmer’s Market is a delightful way to engage with the local community. Held weekly during the summer months, the market features fresh produce, artisanal goods, and handmade crafts from local vendors. It’s a great spot to support local businesses while enjoying the vibrant atmosphere.
The market is filled with the colors and aromas of fresh fruits, vegetables, and flowers. You’ll find a wide variety of items, from organic produce to baked goods and specialty foods. Take the opportunity to chat with farmers and learn about their products.
Live music often accompanies the market, adding to the festive vibe. Families love browsing the stalls and sampling delicious treats while sharing quality time together. It’s an ideal way to spend a morning or afternoon on the island.
When visiting, don’t hesitate to pick up some snacks for a picnic later! The farmer’s market embodies the spirit of community on Martha’s Vineyard, making it a must-do activity.
Address: 20 Kittansett Rd, Oak Bluffs, MA 02557.
18. Kayak or paddleboard in the harbor
Kayaking or paddleboarding in Oak Bluffs Harbor is a fun way to explore the area’s waterways. Rentals are available nearby, making it easy for visitors to get out on the water. Glide over the gentle waves and enjoy a unique perspective of Martha’s Vineyard’s beauty.
As you paddle, keep an eye out for wildlife such as birds, fish, and maybe even seals. The calm waters of the harbor provide a peaceful environment, perfect for beginners and experienced paddlers alike. Explore hidden coves and admire the stunning coastline.
Joining a guided tour can enhance your experience, as instructors share valuable tips and local insights. This activity is a fantastic way to connect with nature and the surrounding scenery while getting some exercise.
After your adventure, consider relaxing on the beach or visiting a nearby café for refreshments. Kayaking or paddleboarding in Oak Bluffs Harbor is an unforgettable activity!
Address: Oak Bluffs Harbor, Oak Bluffs, MA 02557.
19. Explore Mytoi Japanese Gardens on Chappaquiddick Island
Mytoi Japanese Gardens is a serene escape from the bustle of Oak Bluffs. This beautifully landscaped garden on Chappaquiddick Island features winding paths, ponds, and a collection of native plants. Visitors will appreciate the tranquility and peaceful ambiance of this hidden gem.
As you stroll through the gardens, you’ll find carefully arranged features inspired by traditional Japanese design. The harmony of nature is evident in every detail, providing a perfect spot for reflection and relaxation. Be sure to bring your camera to capture the scenic views!
Access to Mytoi can be achieved through a short ferry ride, making the journey part of the adventure. After exploring the gardens, you can enjoy nearby beaches or additional walking trails on Chappaquiddick Island. Make a day of it by packing a picnic to enjoy in the gardens.
A visit to Mytoi is the perfect way to experience the beauty of Martha’s Vineyard while enjoying a tranquil setting.
Address: 41 Mytoi Rd, Edgartown, MA 02539 (Chappaquiddick Island).
20. Go on a scenic whale watching tour
Whale watching tours are an exciting way to connect with nature and experience the waters surrounding Martha’s Vineyard. Various companies offer excursions that provide opportunities to see majestic humpback whales and other marine life in their natural habitat. Tours typically run from spring to early fall.
Guides on board share engaging information about the whales and their behaviors, enhancing the experience. The thrill of spotting a whale breaching or tail slapping is unforgettable. Early mornings can often yield the best views, with clear waters and active marine life.
Bring your camera to capture stunning images of these magnificent creatures against the backdrop of the ocean. Many tours offer amenities such as refreshments and restrooms for added comfort. It’s advisable to book in advance during peak tourist seasons.
Going whale watching is an adventure that people of all ages will cherish. Witnessing these incredible animals in action will create memories that last a lifetime!
Address: Various whale watching tour departure locations.
21. Visit the Oak Bluffs Library
The Oak Bluffs Library is a charming spot for books lovers. Nestled in a picturesque setting, the library provides a welcoming atmosphere for all ages. Whether you’re looking for a quiet place to read or need assistance finding local information, the library is there for you.
In addition to a collection of books covering various topics, the library offers community programs and events often hosted throughout the year. Storytimes for children, book clubs for adults, and art displays are just a few of the activities available.
Relax in one of the comfortable seating areas, and enjoy the cozy ambiance. The staff is friendly and knowledgeable, making it an excellent resource for both locals and visitors. Don’t forget to check out the library’s events calendar during your visit.
Relaxing in the Oak Bluffs Library truly embodies the spirit of learning and exploration, making it a delightful place to visit.
Address: 56 Ryders St, Oak Bluffs, MA 02557.
22. Relax in the Ocean Park
Ocean Park is a beautiful green space that serves as a gathering spot for locals and visitors alike. The park features expansive grassy areas, stunning ocean views, and lovely walking paths. It’s the perfect place to bring a picnic blanket and relax while soaking in the sunshine.
The park also hosts various events during the summer, including live music, community gatherings, and family-friendly activities. You can stroll through the paths and enjoy the beautiful landscaping, which consists of colorful flowers and shaded trees.
Families often enjoy the playground area, where children can safely play while parents unwind in the open space. The proximity to the beach makes it convenient for a post-picnic swim or beach stroll. Overall, Ocean Park is a relaxing and scenic destination in Oak Bluffs, ideal for leisure.
Address: 1 Ocean Park, Oak Bluffs, MA 02557.
23. Enjoy a lighthouse tour at East Chop Lighthouse
East Chop Lighthouse is a stunning landmark that offers a glimpse into the island’s maritime history. Located on a picturesque bluff, the lighthouse has been guiding ships since the 1870s. A visit to this site provides both beautiful scenery and a sense of nostalgia.
While the lighthouse itself is not open for climbing, visitors can take pictures and enjoy the surrounding views. The nearby area features pleasant paths for walking and biking, making it easy to explore the coastline.
Bring a picnic and relax on the grassy areas nearby while taking in the breathtaking views of the ocean. Many people love to watch the boats as they come and go from the harbor. The vibrant sunsets from this location are unforgettable.
Whether you’re a history enthusiast or just looking for a lovely view, a trip to East Chop Lighthouse is an enriching experience on Martha’s Vineyard.
Address: 4 East Chop Drive, Oak Bluffs, MA 02557.
24. Take part in ghost tours or historical walks
Explore the intriguing history of Oak Bluffs through guided ghost tours or historical walks. These excursions provide insight into the island’s past, highlighting legendary stories and charming anecdotes. Expert guides share tales that blend history with a hint of the supernatural.
As you stroll around, you’ll visit notable landmarks and hear fascinating stories about the area’s haunted locations. Ghost tours often feature old inns and historical sites that have captivated the imagination of residents over the years.
On a historical walk, focus on the architecture, culture, and significance of the buildings and neighborhoods. Walking tours create opportunities to learn about the unique culture of Oak Bluffs while enjoying the natural beauty surrounding you.
These tours are suitable for all ages and are perfect for those interested in history and the supernatural. Whether you’re seeking a spooky tale or educational experience, a guided tour will be a memorable part of your visit.
Address: Various starting points depending on the tour company.
25. Experience local shops and boutique stores
Oak Bluffs is filled with local shops and boutique stores offering unique finds and souvenirs. Strolling through the downtown area provides plenty of opportunities to browse arts, crafts, clothing, and more. These shops often feature local artisans and showcase handmade items that reflect the spirit of Martha’s Vineyard.
Don’t miss stopping by bakeries for delicious treats or shops selling fresh produce and gourmet food items. Each store has its own distinct charm and character, adding to the overall shopping experience.
Exploring local shops is a fantastic way to support the community while finding unique items to remember your visit. Engage with the friendly shop owners who often share stories about their products and the island.
After shopping, consider finding a cozy café or restaurant to relax and reflect on your day. Enjoying the local vibes through shopping makes for a well-rounded day of exploring Oak Bluffs.
Address: Various shops and boutiques throughout Oak Bluffs.
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Final Thoughts
Oak Bluffs, Massachusetts, is a vibrant destination that offers a delightful mix of history, culture, and natural beauty. Whether you are exploring the charming streets lined with colorful cottages or enjoying the serene beaches, Oak Bluffs has something for everyone.
From memorable family-friendly activities like the Flying Horses Carousel to serene retreats in the Ocean Park, the area provides a well-rounded experience. Embrace the local culture through art shows and farmer’s markets while indulging in delicious seafood at waterfront restaurants.
Your visit promises beautiful landscapes, rich history, and unforgettable memories that will beckon you to return to Oak Bluffs again. Embrace the charm of Martha’s Vineyard and enjoy everything this lovely community has to offer.