Oak Bluffs Travel Guide

Discover the best things to do, places to stay, and local culture of Oak Bluffs, Massachusetts, with our complete travel guide. Hike, bike, and explore the scenic views and cultural attractions of this charming coastal town.


Introduction to Oak Bluffs

Nestled in the heart of Martha’s Vineyard, Oak Bluffs is a picturesque coastal town in Massachusetts. Known for its charming Victorian architecture, pristine beaches, and vibrant cultural scene, Oak Bluffs is an excellent vacation spot for travelers seeking relaxation and adventure. The town has a rich history and is home to some of the most culturally significant sites in the region. It’s also a popular destination for outdoor enthusiasts, with plenty of opportunities for hiking, biking, and exploring the natural beauty of the island.

List of Places to Visit in Oak Bluffs

Here are the top attractions to visit while you’re in Oak Bluffs:

Culturally Important Attractions: Museums and Historical Places

  • Martha’s Vineyard Museum: This museum showcases the rich history and culture of the island. The exhibits cover everything from the area’s maritime heritage to its role in the Civil War.
  • Flying Horses Carousel: Built in 1876, this national historic landmark is the nation’s oldest operating carousel. It’s a must-visit for anyone visiting Oak Bluffs.
  • Trinity Park: This park is home to the Tabernacle, a 19th-century open-air meetinghouse that hosts religious services and concerts throughout the year.
  • East Chop Lighthouse: Built in 1878, this lighthouse offers stunning views of the Vineyard Sound. Visitors can climb to the top for a panoramic view of the area.

Natural Attractions of Oak Bluffs: Outdoor Adventures and Scenic Views

  • State Beach: Stretching for three miles, this beach is a popular spot for swimming and sunbathing.
  • Oak Bluffs Harbor: This harbor is a bustling center of activity, with boats coming and going all day. Visitors can take boat tours, go fishing, or simply wander around the docks.
  • Oak Bluffs Campground: This collection of colorful gingerbread cottages is a prime example of the Victorian architecture that Oak Bluffs is known for. Take a stroll along the narrow paths between the cottages and soak up the charming atmosphere.
  • Joseph Sylvia State Beach: Located just south of State Beach, this beach offers quieter, less crowded sands and stunning views of the pristine waters and shoreline.

Hiking/Biking Routes of Oak Bluffs

The best way to explore the stunning natural beauty of Oak Bluffs is by hiking or biking. Here are some of the best routes to follow:

  • East Chop Loop: This 4-mile loop offers panoramic views of the harbor and the Nantucket Sound. The route takes you through quiet roads and quaint neighborhoods.
  • The State Forest: This forest covers almost 6,000 acres and has over 20 miles of trails that wind through the hills and wetlands of the area.
  • Vineyard Trust Trails: The Vineyard Trust oversees a network of hiking trails that boast fantastic views of the island. The trails range in difficulty, so there’s something for everyone.

Best Things to Do in Oak Bluffs: Activities and Tours

Whether you’re traveling solo or with family and friends, Oak Bluffs has plenty of activities to keep you entertained. Here are some of the best things to do in the town:

  • Take a Boat Tour: Explore Oak Bluffs from a different perspective by taking a boat tour of the area. These tours allow you to see the town and the surrounding islands from the water, offering a unique perspective.
  • Go Fishing: Oak Bluffs is renowned for its excellent fishing opportunities. Hire a fishing guide for a day to explore the best spots and try to catch some fish.
  • Attend a Concert: The Tabernacle in Trinity Park is a popular venue for concerts and events. Check the calendar to see if there are any shows you’d like to attend.
  • Visit Local Wineries: The Martha’s Vineyard is home to several vineyards and wineries. Take a tour of the vineyards, learn about the wine-making process, and sample some of the delicious local wines.

Week-Long Itinerary for Oak Bluffs

If you’re planning on spending a week in Oak Bluffs, here’s a sample itinerary to help you make the most of your time:

Day 1: Arrive in Oak Bluffs and spend the day exploring the town center and harbor area.

Day 2: Hike or bike through the State Forest and enjoy a picnic lunch.

Day 3: Take a boat tour around the island, stopping at local lighthouses and fishing spots.

Day 4: Visit the Martha’s Vineyard Museum and learn about the history and culture of the island.

Day 5: Spend the day at State Beach, swimming and sunbathing.

Day 6: Take a drive to nearby Chappaquiddick Island and explore the beaches and wildlife areas.

Day 7: Attend a concert at the Tabernacle in Trinity Park and enjoy a local wine tasting.

Food and Drink Scene of Oak Bluffs

Oak Bluffs is home to numerous restaurants and bars, with cuisine ranging from seafood to international flavors. Here are some must-try dishes and local beverages:

Must-Try Dishes

  • Lobster Rolls: These classic New England sandwiches are a staple of the region. Try one at the Lobsta Trap, a local restaurant that is known for its excellent seafood.
  • Clam Chowder: Another New England classic, clam chowder is a rich, creamy soup made with fresh clams. Head to the Lookout Tavern for a taste of this iconic dish.
  • Catch of the Day: Many local restaurants offer a daily catch, featuring fresh fish that was caught that morning.

Local Beverages

  • Martha’s Vineyard Wine: The Vineyard is home to several vineyards, producing superb wines from local grapes.
  • Bad Martha Beer: This local brewery produces a range of delicious beers, including oak-aged stouts and fruity IPAs.

Where to Stay in Oak Bluffs: Hotels, Hostels, and Guesthouses

Oak Bluffs has a range of accommodation options, depending on your budget and preferences. Here are some of the best places to stay in the town:

  • The Ocean View Inn: This historic inn offers breathtaking views of the ocean and easy access to the town center.
  • Pequot Hotel: This classic New England hotel has been welcoming guests for over 100 years. It’s located just a short walk from the beach and the town center.
  • Isabelle’s Beach House: This charming guesthouse is located on the beach and offers luxurious accommodations and personalized service.

What to Buy in Oak Bluffs: Souvenirs and Local Products to Bring Home

Oak Bluffs has several shops and boutiques selling souvenirs and locally produced goods. Here are some of the best things to buy in the town:

  • Antiques and Collectibles: Oak Bluffs is home to several antique shops, offering a unique selection of vintage furniture and curiosities.
  • Handmade Crafts: The island has a vibrant community of artisans, producing everything from pottery to jewelry.
  • Mineral and Gemstones: The Martha’s Vineyard is home to several mines, producing high-quality gemstones and minerals. Check out the Alley’s General Store for a selection of local stones.

Local Culture and Customs of Oak Bluffs

Oak Bluffs has a rich cultural heritage, shaped by its history as a port town and its location on the outskirts of New England. The town has a laid-back vibe, with a focus on relaxation and enjoying life’s simple pleasures. Visitors should be respectful of the local customs and traditions, such as the practice of allowing drivers to cross the street before making left-hand turns, and the importance of conservation and sustainability in the local community.

Best Time to Visit Oak Bluffs

The best time to visit Oak Bluffs is during the summer months, from June to September. This is when the weather is warmest, and visitors can enjoy the beaches and outdoor attractions to the fullest. However, this is also the busiest time of year, with lots of tourists and higher prices. If you’re looking to avoid the crowds, consider visiting in the shoulder season, from April to May or September to November.

Do’s and Don’ts of Oak Bluffs

Do:

  • Do take a boat tour of the area
  • Do explore the State Forest by bike or foot
  • Do attend a concert at the Tabernacle in Trinity Park
  • Do try the local seafood and wine
  • Do respect the local culture and customs of Oak Bluffs

Don’t:

  • Don’t forget to bring sunscreen and insect repellent when exploring the outdoors
  • Don’t litter or leave trash on the beaches or hiking trails
  • Don’t drive recklessly or speed in residential areas
  • Don’t forget to tip your servers and tour guides
  • Don’t forget to book your accommodations in advance, especially in peak season.

Safety and Health

Safety in Oak Bluffs

Oak Bluffs is a safe and welcoming community, with a low crime rate and friendly locals. However, visitors should still exercise caution and take standard safety precautions, such as locking their vehicles and securing their valuables. The town has an excellent police department and emergency services, and visitors can feel confident in their ability to respond to any emergencies.

Health in Oak Bluffs

Oak Bluffs has several medical clinics and pharmacies, offering a range of health services to residents and visitors. Visitors should be aware of the dangers of tick-borne illnesses, such as Lyme disease, and should take precautions when exploring the outdoors, such as wearing long sleeves and pants and using insect repellent.

Getting to Oak Bluffs: Transportation Options and Logistics

Oak Bluffs is located on the island of Martha’s Vineyard, which is accessed by ferry or airplane.

Airports Near Oak Bluffs

The closest airport to Oak Bluffs is Martha’s Vineyard Airport, with daily flights from Boston, New York, and other East coast cities.

Bus Stations Near Oak Bluffs

Peter Pan Bus Lines and Greyhound offer bus services to Martha’s Vineyard, with stops in nearby towns such as Falmouth and New Bedford.

Other Options

Visitors can also access the island via ferry from several nearby towns, including Woods Hole, Hyannis, and Falmouth. The Steamship Authority and the Island Queen are the primary ferry operators.

How to Get Around in Oak Bluffs

Oak Bluffs is a small town, and many of the attractions are within walking distance of each other. Alternatively, visitors can rent bikes or take taxis or Ubers to get around town.

Where to Go Next from Oak Bluffs: Nearby Destinations and Excursions

While Oak Bluffs has plenty to offer visitors, there are also several nearby destinations and excursions to explore. Here are some of the best places to visit after leaving Oak Bluffs:

  • Edgartown: This picturesque village is just a short drive from Oak Bluffs and is known for its historic buildings and sailing culture.
  • Aquinnah Cliffs: These towering cliffs offer stunning views of the Atlantic Ocean. Visitors can hike along the trails or take a guided tour.
  • Menemsha Beach: This beach offers stunning sunset views and excellent seafood restaurants. It’s a great spot for a romantic evening or a family picnic.

Conclusion

Oak Bluffs is a charming coastal town with a rich history and stunning natural beauty. Whether you’re interested in exploring the cultural attractions, outdoor adventures, or simply enjoying the laid-back pace of life, Oak Bluffs has something for everyone. From hiking and biking to wine tasting and shopping, there’s no shortage of activities to keep you entertained during your visit. So pack your bags and start planning your trip to this idyllic seaside town today!