Top 10 Family-Friendly Activities in Oak Bluffs

Welcome to Oak Bluffs, a charming town located on Martha’s Vineyard. Pink Rock Rentals, a delightful pink cottage nestled at the heart of town, invites you to explore the top 10 family-friendly activities in the Oak Bluffs. Whether your family is full of thrill-seekers or beach lovers, Oak Bluffs offers something for everyone.

Ryan Family Amusements

Start your Oak Bluffs adventure with a visit to Ryan Family Amusements. This family entertainment center offers a variety of exciting games and activities for all ages. 


Challenge your family to a friendly round of bowing, test your skills at the game room, and win some souvenirs at the prize counter!  Ryan Family Amusements guarantees a fun-filled experience for the whole family. 

Joseph Sylvia State Beach

Called the “Bend-In-The-Road” beach, the Joseph Sylvia State Beach is a beautiful, two-mile stretch of sandy shoreline. Full of low dunes, plenty of seashells, and mild waves, a visit to this family-friendly beach is perfect for a sunny afternoon!

Flying Horses Carousel

Take a step back in time and visit the historic Flying Horses Carousel, the oldest operating carousel in the United States. Adorned with vibrant hand-painted horses, this enchanting ride delights children and adults alike. Don't forget to try your luck at grabbing the brass ring for a free ride—an Oak Bluffs tradition!

Circuit Avenue

Stroll down Circuit Avenue, the vibrant heart of Oak Bluffs. This lively enclave is full of unique shops, boutiques, and eateries, offering a delightful shopping and dining experience for the whole family. Explore local crafts, indulge in delicious ice cream, or pick up souvenirs to commemorate your Oak Bluffs vacation.

Ocean Park

If you want to escape the hustle and bustle of daily visit, visit Ocean Park. This tranquil oasis is located just a few steps from Circuit Avenue and is surrounded by beautiful Victorian mansions. Let the kids run free on the open lawns, have a picnic in the gazebo, or simply relax in the serene surroundings. 

Gingerbread Houses in Oak Bluffs Campgrounds

Immerse yourself in the whimsical charm of the Campgrounds, home to Oak Bluffs' iconic gingerbread houses. These colorful cottages feature intricate architectural details and are a delight to explore. Take a leisurely walk with your family, marvel at the unique designs, and capture the perfect Instagram-worthy snapshots. Our cottage is actually one of the Gingerbread Cottages!

Manuel Correllus State Forest

The Manuel Correllus State Forest is perfect for an outdoor adventure. Spanning over 5,000 acres, the forest is full of hiking trails, biking paths, and diverse flora. The forest is a great place to pack a picnic, admire the rich nature of Oak Bluffs, and spend quality time with your family. 

Cottage Museum

You said you can’t learn on vacation? Visit the Cottage Museum, a quaint historic site that will give you a window into the past, specifically focusing on the fascinating history of the Methodist Camp movement that took place in Oak Bluffs during the late 19th century. 

Oak Bluffs Public Library

Escape into the world of books at the Oak Bluffs Public Library. This inviting space offers a dedicated children's section, complete with engaging activities, storytime sessions, and a wide range of books for young readers. Encourage your children's love for reading and spend a relaxing afternoon exploring the library together.

East Chop Lighthouse

Top off your trip with a visit to the iconic East Chop Lighthouse. The lighthouse is a nice walk from downtown Oak Bluffs and is situated on the highest protruding bluff on Martha’s Vineyard. Climb all the way to the top and enjoy the panoramic views of Martha’s Vineyard and the surrounding ocean. 


Oak Bluffs provides a perfect blend of natural beauty, historical charm, and family-friendly activities. Pack your bags, embark on an adventure, and let the magic of Oak Bluffs captivate your entire family!

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