There is truly no other place in the world like Martha’s Vineyard. This unique island situated in New England, is made up of small towns, including the welcoming area of Oak Bluffs.
The colorful and historic town of Oak Bluffs is one of the liveliest on the island. There is so much to see and do, especially during the fall season. Plus, you can avoid the hoards of people that flock to the area during the summertime.
Up until now, I had only visited Martha’s Vineyard in the summer, so getting to experience the island during off-season, was a treat. I have a knack for seeking out destinations in their off-season to get a more authentic and special experience.
Oak Bluffs is a fantastic fall destination for families, couples, and solo travelers, who are looking for a picturesque getaway that is more laidback. I’ve put together this travel guide to help you make the most of your time in Oak Bluffs, so that you can discover all the wonderful things that await you.
Oak Bluffs Fall Travel Guide
Where Is Oak Bluffs Located?
Oak Bluffs is a quiet resort community situated on the northeast shore of Martha’s Vineyard. Martha’s Vineyard is a 100 square mile island located just three miles off the coast of Cape Cod in Massachusetts. The island is populated by year-round residents, seasonal residents, and hundreds of thousands of visitors and tourists.
Oak Bluffs was named Cottage City in 1880 before it became Oak Bluffs in 1907. The 7.37 square mile town of Oak Bluffs is part of Dukes County, Massachusetts.
Traveling south on scenic Beach Road will take you from Oak Bluffs to Edgartown. Vineyard Haven and West Tisbury are a short driving distance away, with Nantucket Sound just a bit further northeast.
How To Get To Oak Bluffs MA
By Ferry
Most people, visitors and locals included, take the Ferry from Woods Hold on Cape Cod to get to Oak Bluffs on Martha’s Vineyard. There is a year-round passenger service from Woods Hole via the Steamship Authority.
These ferries follow a regular schedule, running for almost the whole day. They offer wifi and refreshments for the 7-mile, 45-minute trip. There is indoor and outdoor seating. If you plan on traveling with a vehicle, you’ll need to make a reservation in advance. Passenger reservations aren’t necessary.
There are also several private ferry companies offering in-season services. If you’re bringing your pet with you, you’re welcome to bring them onboard the Steamship Authority and private ferries, as long as they’re on a leash or in a crate.
By Car
Because Martha’s Vineyard is an island, there’s no direct road from Boston. If you want to travel by car, you’ll need to drive to Cape Cod’s ferry terminals. The main port for the Steamship Authority passenger ferry, Woods Hole, allows you to bring your vehicle onto the ferry as long as you make a reservation ahead of time.
By Plane
The easiest and most efficient, but also the most expensive, way to get to Martha’s Vineyard from Boston is by plane. This option is especially helpful for those who suffer from seasickness. Cape Air has daily flights to and from Boston’s Logan International airport and Martha’s Vineyard airport all year long. The flight is only 40 minutes.
JetBlue also offers seasonal nonstop flights from Logan International airport to Martha’s Vineyard. There are also direct nonstop flights from New York City on JetBlue and Delta Airlines.
Travelers can also book a scheduled nonstop service on Tradewind airlines, or book a private charter flight from practically anywhere.
Things To Do In Oak Bluffs
Ocean Park
There are few places as beautiful as Ocean Park in the fall. The gorgeous fall foliage, picturesque gazebo, and elaborate, Victorian-style houses look like they were plucked right off of a movie set. Go for an afternoon stroll, enjoy a picnic lunch, and, if you’re visiting in August, cozy up to watch the Ocean Park fireworks show.
Click here for directions.
Inkwell Beach
Inkwell Beach is the most conveniently located beach in Oak Bluffs. You’ll find it right off of Seaview Avenue, near Ocean Park. It’s also just a short walk from the ferry dock.
Inkwell Beach is covered with soft, fine sand that will warm your toes during the day and cool them off at night.
Click here for directions.
Sunset Lake
A lakeview sunset over the harbor? Yes, please! I bet you can already guess where the lake gets its name – the beautiful sunsets. Grab a picnic basket and your favorite bottle of wine, and spend some time snacking and relaxing by the lake. Or better yet, take a comfortable and easy-going walk around the lake while taking in the nature.
Click here for directions.
Gingerbread Houses/Cottages
The iconic gingerbread cottages at Oak Bluffs Campground are an absolute must-see. What used to be a Methodist camp meeting location is now a National Historic Landmark. The cottages, which were built in the 19th century, look like storybook gingerbread houses because of their small size, picket fences, and delicate trim. Individual cottages are privately owned so you usually can’t explore their interiors, but they’re still a wonderful sight to see from the street.
Click here for directions.
Shopping On Circuit Avenue
The one way street of Circuit Avenue is bustling with people throughout the year, but it’s especially busy in the summer and fall. People come from all over to visit the restaurants, ice cream and coffee shops, bars, boutiques, and clothing stores.
During my trip, I visited Island Outfitters and Stefanie Wolf Designs for a wonderful shopping experience.
Island Outfitters is a laid-back, costal-style clothing store, with a plethora of options to choose from between clothes and accessories, in every season. I picked out a cozy cream-colored fall sweater that I had been searching for!
Stefanie Wolf Designs focuses on gorgeous artisan jewelry pieces and offers an array of accessories to choose from. The Long Beaded Necklace with 7 different ways to wear it is one of their most popular products. They are absolutely stunning in person and there’s a ton of different colors to choose from.
The store also offers Snowflake Parties where you can secure a fun evening with your friends and family during the holidays!
Click here for directions.
Ryan Family Amusements
When you are ready for a break from shopping along Circuit Avenue, look to The Ryan Family Amusements for all kinds of fun and entertainment. You can enjoy video games, prize games, and arcade games, as well as ten-pin and candlepin bowling alleys. If you’re traveling with kids, this is an especially great place to spend some time while you’re in Oak Bluffs.
Click here for directions.
Joseph Sylvia State Beach
As you drive down Beach Road between Oak Bluffs and Edgartown, you’ll be surrounded by miles of beautiful sandy beach. Known as State Beach, swimmers especially love this destination because of its slow, gentle waves and gradual drop-off. Whether you’re going for a swim, walking along the shore, or watching the waves roll in, Joseph Sylvia State Beach is worth seeing in person.
Click here for directions.
Flying Horses Carousel
The Flying Horses Carousel is one of the most historic attractions in Oak Bluffs. This beloved national landmark was first built in 1876 and operated on Coney Island before it was moved to Oak Bluffs in 1884. In 1986, the Preservation Trust acquired the carousel and conducted an extensive restoration that updated the attraction while keeping the original horsehair manes and tails and glass eyes.
The Flying Horses Carousel is the oldest platform carousel in the United States. It still operates during the summer months and remains a beautiful sight to behold throughout the rest of the year.
While the carousel is closed during off-season, it’s worth taking a peak through the window or keeping in mind for a summer trip. I experienced the Flying Horses as a kid and will never forget it! In fact, I kept the golden ring that I won in my room for years. I wonder where that went…
Click here for directions.
Jaws Bridge
Best known for its appearance in the movie Jaws, the American Legion Memorial Bridge is another well-known attraction found in Oak Bluffs. The bridge is located on Beach Road, connecting Edgartown and Oak Bluffs and is a popular destination for any movie-buff tourist or traveler. Snap a couple photos and enjoy the view, but keep in mind that it is illegal to jump off of this bridge or to impede traffic. Not that you’d be jumping off the bridge in the Fall anyway.
Click here for directions.
West Chop Lighthouse
If you’re a big fan of history, the West Chop Lighthouse is a must-visit. With history dating back to the early 1800’s, the energy from the past is almost palpable in the air. And the view isn’t too shabby either. The lighthouse station is located at the entrance of Vineyard Haven Harbor in Tisbury, Massachusetts. It’s on the northern tip of West Chop, a few miles from the village of Vineyard Haven, making it an easy stop along your route.
Click here for directions.
Farm Neck Golf Club
If a round or two of golf sounds like the perfect way to spend one of your vacation days, look no further than Farm Neck Golf Club. This premier golfing location offers beautiful views as you partake in the various amenities, including lessons, clinics, junior golf, and tournaments. There are even six outdoor tennis courts if you want a break from the putting green. Plus, once you work up an appetite, you can chow down at the Farm Neck Cafe.
Click here for directions.
Felix Neck Wildlife Sanctuary
The Felix Neck Wildlife Sanctuary is a great place to visit to appreciate the beauty of local wildlife and habitat. At the sanctuary, you can participate in hiking, educational tours, and wildlife photography. You can even kayak on the Sengekontacket Pond.
There are four miles of trails that lead you past ponds, woodlands, meadows, salt marshes, and shorelines. The sanctuary is a wonderful place to spend an afternoon on Martha’s Vineyard.
Click here for directions.
Manuel F. Correllus State Forest
Another way to explore and enjoy the great outdoors while on the island is to visit the Manuel F. Correllus State Forest. This expansive natural attraction features 5,300 acres of forest and natural landscape.
You can also visit The Heath Hen statue in the middle of the park. The statue was built to honor the bird that used to live in the state forest before going extinct in 1932.
Click here for directions.
Louisa Gould Art Gallery
If you like to take time appreciating the finer things in life, you may want to check out the Louisa Gould Art Gallery. Louisa Gould is an artist from Vineyard Haven who became famous for her contemporary photography and unique abstract artwork.
Louisa Gould’s gallery near Oak Bluffs has been operating for 18 years. Tourists and locals love to stop by and take a closer look at her masterpieces, both new and old. You can also check out exhibits from emerging local and regional artists.
Click here for directions.
Pecoy Point Preserve
Yet another natural attraction worth seeing is the Pecoy Point Preserve. Nature lovers, wildlife enthusiasts, and curious-minded visitors will appreciate the salt marshes, freshwater pond, and grasslands that make up the preserve. You may even catch a glimpse of some migratory birds as well as local birds and other animals.
Activities at the preserve include hiking, horseback riding, mountain biking, picnicking, boating, and kayaking.
Click here for directions.
Best Restaurants In Oak Bluffs
Aalia’s Coffee
Aalia’s Coffee just had its first season in business and quickly became a favorite among locals and visitors. Here, you’ll find so much more than just a standard cup of coffee. You’ll enjoy browsing the diverse menu of beverages and tasty eats that you’ll only find at this local spot.
Click here for directions.
Dos Mas
Following the success of BackYard Taco, a small taqueria in Edgartown, brothers Evan and Zared and their father Raphael opened a second location – Dos Mas. Dos Mas is now the place to go for hand-pressed tortillas, fresh spicy margaritas, and an upbeat, lively atmosphere.
Click here to take a look at the menu. Click here for directions.
Offshore Ale
Offshore Ale has been serving Oak Bluffs locals and visitors since 1997. This casual establishment is known for its award-winning craft beers and familiar, hearty meals.
Offshore Ale is Martha’s Vineyard’s first and only brewpub. Here, you can expect classic brewpub favorites like fish and chips, steamed mussels, thin-crust pizzas, and more. The nine beer taps rotate seasonally so there’s something new to try every time you stop by.
Click here to take a look at the menu. Click here for directions.
MV Chowder Company
Martha’s Vineyard Chowder Company is a casual dining spot known for its remarkably delicious, award-winning clam chowder. Patrons can also choose from a wide selection of cooked and raw seafood, and arguably the best lobster rolls in the area.
Click here to take a look at the menu. Click here for directions.
The Ritz MV Dive Bar
A beloved spot for locals and tourists, The Ritz is an iconic dive bar in the Oak Bluffs area of Martha’s Vineyard. This a comfortable, casual joint that warmly welcomes anyone looking for good food, strong drinks, and plenty of live music.
Click here to take a look at the menu. Click here for directions.
Sand Bar and Grille
You can expect fresh sushi and traditional American bar food at the Sand Bar and Grille in Oak Bluffs. The Sandbar, as it’s commonly known, is located right on Oak Bluffs harbor and just steps from the ferry. It’s a great spot for tasty food and a fantastic, fun atmosphere.
Click here to take a look at the menu. Click here for directions.
Fat Ronnie’s Burger Bar
Ronnie has been “perfecting the craft of burger making” since he was 6 years old. In 2013, using his grandmother’s mouth watering recipes with a modern twist, Ronnie opened Fat Ronnie’s Burger Bar. This build-your-own burger joint has since become a favorite among locals and tourists alike.
Click here to take a look at the menu. Click here for directions.
The Sweet Life Cafe
Often touted as one of the best, if not the best restaurant in Martha’s Vineyard, The Sweet Life Cafe is an upscale dining destination you just have to try for yourself. This New American restaurant blends classic culinary tradition and modern day techniques to make delicious dishes and innovative beverages. The frequently-changing menu and their cocktail and wine lists are sure to impress.
Click here to take a look at the menu. Click here for directions.
Chef Deon’s Kitchen
If you love seafood but want something a little different than traditional New England flavor, you’re going to want to head to Chef Deon’s Kitchen in the local VFW hall. Jamaica-born Chef Deon has been serving up Caribbean cuisine for years. With delicious food and, often, live music, this is one hidden gem you’re going to want to visit.
Click here to take a look at the menu. Click here for directions.
The Red Cat Kitchen
The Red Cat Kitchen is a farm-to-table, sea-to-table restaurant that has been serving delectable local fare in Oak Bluffs for 11 seasons. While there is indoor and outdoor dining available, as well as bar seating, they usually fill up fast so they recommend you call in advance (508-696-6040) to make a reservation.
Click here to take a look at their menu. Click here for directions.
The Barn Bowl & Bistro
Barn Bowl and Bistro is another Oak Bluffs restaurant that is frequently mentioned among the best in Martha’s Vineyard. The Barn is a great place for families, couples, groups, and more. Here, you’ll find some of the more creatively-topped pizzas, as well as wings, curry mussels, and plenty of classic bar foods.
In addition to their impressive beer selection, The Barn has a 10-lane ten-pin bowling alley and a good amount of outdoor seating.
Click here to take a look at their menu. Click here to get directions.
Best Places To Stay In Oak Bluffs
The Morgan Hotel
Nestled in beautiful Oak Bluffs, The Morgan Hotel is arguably the best place to stay when visiting Martha’s Vineyard. This newly renovated hotel is walking distance from several notable monuments including America’s First Carousel, The Flying Horses, and the African American Heritage Trail.
The Morgan Hotel in Oak Bluffs is in a prime location within walking distance to all the major attractions, shops and restaurants! Aside from the ideal location, the check in process is completely self-oriented and you can access the hotel building and your room through an app on your phone. I always love contactless check ins as it makes the whole process quicker and smoother.
The rooms are small, quaint and coastal with some offering amazing views of the ocean where you can watch the sunrise.
The Morgan Hotel has welcomed overnight guests since 1873. It is now an updated 14-room boutique hotel with several room types and amenities that include:
- High speed wireless internet access for unlimited devices
- Bedside iHome Bluetooth docking stations with USB charging
- Complimentary toiletries
- 43” flat screen HDTV with streaming capabilities
Click here to book your stay at The Morgan Hotel. Click here for directions.
Oak Bluffs Inn
Oak Bluffs Inn is a locally owned, award-winning hotel that combines old world style and modern amenities. The Inn is located downtown and within walking distance to the beach, local shops and boutiques, and restaurants.
Erik and Rhonda have been the innkeepers for 21 years and offer expert advice on how to make the most of your island vacation.
There are ten, individually decorated rooms available for guests of The Oak Bluffs Inn, including a child-friendly first-floor room and the penthouse which is a lot more like an apartment than a hotel room. Staying at the Oak Bluffs Inn gives you access to several amenities, including:
- Air conditioning
- Private baths
- Continental breakfast (May 1 – Oct 31)
- Complimentary snacks and beverages
- Off-street parking
- Outdoor patio
- Frette linens
- Wrap around porch
- Aveda toiletries
- Free wifi
- Firepit
- Bike rack and floor pump
- Refrigerators (in most rooms)
Click here to book your stay at Oak Bluffs Inn. Click here for directions.
The Dockside Inn
The Dockside Inn is situated on the stunning Oak Bluffs Harbor. It’s a boutique-style hotel that blends award-winning modern design with fun nautical decor and modern amenities. In 2012, The Dockside Inn, under new ownership, was completely renovated and updated.
There are 22 rooms available. Guests can enjoy complimentary ice cream treats and fresh baked cookies every afternoon, as well as the following hotel amenities:
- High quality thread count duvet covers and linens
- Private bath with tub/shower
- In-room heat and air conditioning
- Flat-screen television
- Iron and hair dryer
- iHome radio/alarm clock
- Black out shades for privacy and sleeping in
- Complimentary bottled water
- Outdoor seating area
- Complimentary wifi
- Complimentary ice
- Use of beach gear (including beach chairs, umbrellas, coolers, toys, towels, etc.)
Guests also have access to the following services, free of charge, from 7 AM to 10 PM.
- A fully stocked snack bar that pretzels, chips, fresh baked pastries, fresh baked cookies, coffee, snacks, ice cream and popsicles
- A Hot Springs sauna and a 6 person hot tub
- An outdoor shower with rain head, foot jets and back massager
- A second floor roof-top sun deck
- A courtyard seating area in the garden
Click here to book your stay at The Dockside Inn. Click here for directions.
Inkwell Beach House
Inkwell Beach House, formerly known as Isabelle’s Beach house, is a classic Victorian beach cottage overlooking Inkwell Beach. The locally owned Inkwell Beach House is the perfect destination for guests who want to immerse themselves in the island’s unique and colorful community.
There are 12 different rooms in the guest house, including family studios, an apartment, and guest rooms of various sizes. Each room has an en-suite bathroom. There are rooms on three floors, but no elevator, so you’ll need to be comfortable with stairs to stay on the top floor.
Inkwell Beach House is open year-round. Full house rentals are available in the winter months. To ensure the comfort of each guest, Inkwell Beach House provides the following amenities:
- Cable TV with pay-per-view movies
- Complimentary high-speed internet access
- Standard bath amenities
- Beach towels (upon request)
- Complimentary continental breakfast from 8 AM to 10 AM
- Tea, coffee, and snacks on the porch or in the lobby lounge
- Bike rentals
Click here to book your stay at Inkwell Beach House. Click here for directions.
Pequot Hotel
Another fantastic lodging option in Oak Bluffs is the Pequot Hotel. This historic hotel has been a favorite in Oak Bluffs for nearly 100 years. Guests come from all over to relax and enjoy the coastal atmosphere of Martha’s Vineyard. The Pequot Hotel is walking distance from the ferry, one block from the beach, and three blocks from town.
A perk of staying at the Pequot Hotel that guests tend to mention the most is the complimentary iced tea, lemonade, and fresh baked cookies that you can enjoy while sitting in a classic rocking chair on the front porch.
Guests can also expect the following amenities:
- Complimentary continental breakfast buffet (with freshly baked muffins)
- Complimentary iced tea, lemonade, and fresh baked cookies every afternoon (with complimentary mimosas on Sunday mornings)
- Complimentary WiFi throughout the hotel
- Private baths with Gilchrist & Soames toiletries
- Local, knowledgeable, super-friendly staff
- Complimentary beach towels and beach umbrellas to borrow (first come, first served)
- Bike rentals delivered to hotel
- Computer for guest use
- Outdoor shower in back garden
- Housekeeping with environmentally-friendly Deirdre Imus “Greening the Cleaning” products
- Friday evening porch parties
- Cozy gas fireplace and large flat-screen TV in the common room
Click here to book your stay at The Pequot Hotel. Click here for directions.
Martha’s Vineyard Surfside Hotel
The Surfside Hotel in Martha’s Vineyard, a premier hotel in Oak Bluffs, has been family owned and operated since 1987. MV’s Surfside Hotel was named a 2022 Traveler’s Choice Hotel by Tripadvisor.
The Surfside Hotel is perfectly situated near Oak Bluffs Harbor, Circuit Avenue, and the Sound, with cafes, shopping, and fine dining within walking distance. There are numerous rooms available, including suites with a king size or queen size bed in the bedroom and a daybed and a twin trundle bed in the adjoining living room.
Guests have access to the following amenities:
- Air-conditioning, heat, cable TV, an iron and ironing board, and a mini-fridge in each room
- Free wifi
- Microwaves and coffee makers in select rooms
- Two-person soaking tubs in all suites
- Pack-N-Play cribs available at no charge.
- Roll-away beds are only available in some rooms (+$25 per night)
- Well-trained pets and responsible pet owners are welcome for a small additional nightly charge
- Beach chairs, beach towels, and umbrellas available for guests to rent from the front desk
- Overnight parking for $30 per night
Click here to book your stay at The Surfside Hotel. Click here for directions.
Summercamp
Summercamp Hotel is the largest ocean-front hotel on Martha’s Vineyard. The gorgeous, vibrantly adorned hotel on Martha’s Vineyard is located in the center of Oak Bluffs, which makes it easy for guests to explore all that the town has to offer. Summercamp has been fully renovated with modern adornments and amenities, to offer guests a truly unique place to stay.
Per Summercamp’s website, the hotel was designed to give guests “the chance to relive the glorious days of childhood summers–while also enjoying the amenities of adulthood.”
There are 95 rooms available, with amenities that include:
- Modern rooms and suites with incredibly soft linens and fun decor
- Large porches and balconies with harbor views and rocking chairs
- Combination game and rentable function room with ping pong, games, television, and more
- A Camp Canteen with snacks and sodas for sale
- Spacious guest lounge
- Lather bath amenities
- Tivoli radios with Bluetooth and USB charging outlets in every room
- LED Smart TVs
- In-room refrigerators
- Hospitality Stations with filtered still and sparkling water, Keurig coffee and tea
- Free wireless internet
- Waffle Kimono robes
- Room essentials, such as wine glasses, corkscrews, irons, hairdryers, and more
- 24-hour front desk
- Complimentary daily housekeeping services
- Personalized concierge services
Click here to book your stay at the Summercamp Hotel. Click here for directions.
Madison Inn
The Madison Inn in Oak Bluffs is another beautiful seaside hotel. This locally-owned and operated inn is literally steps away from the gorgeous waters of Nantucket Sound and walking distance to the ferry.
The Madison Inn has been a Tripadvisor Travelers Choice selection every year, for the last ten years. There are 15 rooms available with various accommodations. Guests have access to the following hotel amenities:
- Guest microwave and refrigerator located off the lobby
- Freezer filled with complimentary ice pops and ice cream bars
- Beach toys, towels, chairs, and umbrellas
- A secure room to store bikes
- Portable Coleman coolers in various sizes
- Readily available ice
- Board games to borrow
- Filtered cold and hot water dispenser by the coffee bar
- Keurig coffee machine with a multitude of coffee choices located at the coffee bar
- A selection of granola bars and fresh fruit is available throughout the day
- Baked bread from Morning Glory Farm or Coffee Cake in the morning
- Luggage storage before and after check-in and check-out
- Free wifi throughout the property
- Bricked courtyard area for reading or sipping morning coffee
Room amenities for guests include:
- Air conditioning
- Bluetooth audio dock with charger
- LectroFan white noise machine
- Complimentary bottles of water
- Complimentary bags of Cape Cod potato chips
- Flatscreen cable TV
- Toiletries from Roam
- Hairdryer
Click here to book your stay at the Madison Inn. Click here for directions.
The Narragansett House
The 150 year old Victorian rooms of the Narragansett House have a distinct, unique style that can only be found in Oak Bluffs. There are rooms of various sizes to accommodate different guests, as well as modern furniture and vintage decor for ultimate comfort.
According to the Narragansett House website, “room prices vary based on size of the room, size of the bed, the seasonal demand and room amenities which vary.”
The following amenities are offered to guests of Narragansett House:
- Free wifi
- Air conditioning unit in each room
- Complimentary toiletries
- TV in select rooms
- Fridge in select rooms
- Beach towels upon request
- Complimentary breakfast on the porch
Click here to book your stay at Narragansett House. Click here for directions.
Best Time To Visit Martha’s Vineyard
While summertime is busiest in Martha’s Vineyard, there’s still plenty to do and see on the island in the fall. September is a particularly wonderful time to visit, and October is a fantastic time to come too. As the crowds dissipate, the town quiets down, and it’s much easier to get around and participate in local activities. You’ll have an easier time booking a stay at one of the local historic homes. Even the ferry ride is less crowded.
Come and see what all awaits you in Oak Bluffs this fall!
There are areas scattered throughout New England that feel extra special during certain times of the year. For me, that’s Oak Bluffs in the fall. There’s truly no other place like it and I hope you get to experience it for yourself.
If you’ve already been there, I’d love to hear about your visit and your favorite things to do while there! To read more about my own traveling adventures, head on over to my blog.
Happy Travels xx
