Family Fun in Downtown Oak Bluffs (That Adults Will Love Too!)
One of the best things about staying at the Oak Bluffs Inn is that so many family-friendly activities are just a short walk from our front door. You can leave the car parked and spend the day exploring downtown together. While these activities are perfect for kids, don’t be surprised if the adults end up having just as much fun.
Take a Ride on the Flying Horses
No visit to Oak Bluffs is complete without a ride on the Flying Horses Carousel, the oldest operating carousel in the United States. This beautifully restored carousel has been delighting families since the 1800s, and riding the hand-carved horses is a Martha’s Vineyard tradition.
The Flying Horses is owned and lovingly maintained by the Martha’s Vineyard Preservation Trust, the same organization that cares for Union Chapel, one of Oak Bluffs’ most recognizable landmarks that we featured in an earlier blog post. Their stewardship helps preserve these treasured pieces of the Island’s history for future generations to enjoy.
The real challenge? Trying to catch the famous brass ring. As the carousel spins, riders reach for rings from a dispenser. Grab the brass ring, and you’ve earned a free ride! It’s a game that has been entertaining generations of visitors, and it’s just as exciting for parents as it is for kids.
Pick Up Toys for Ocean Park
A few doors away, you’ll find two favorite downtown shops: The Corner Store and The Lazy Frog.
These stores are filled with classic summer fun:
- Colorful kites
- Beach games
- Frisbees
- Bubble wands
- Sand toys
- Classic balsa wood airplanes
The Corner Store 
The Lazy Frog
After shopping, head across the street to Ocean Park. Its wide-open lawn is the perfect place to fly a kite or launch a balsa airplane on an afternoon sea breeze. Many parents find themselves joining in the fun before long!
Play at Niantic Park
Just a short walk from downtown is Niantic Park, one of Oak Bluffs’ favorite playgrounds.
This beautiful playground was built by the community and offers climbing structures, swings, slides, and plenty of room for kids to burn off energy. It’s a wonderful stop after breakfast or before dinner.
An added bonus for families: public restrooms are located right at the park, making it an easy stop during a day of exploring.
Spend the Evening at Ryan Family Amusements
As the sun begins to set, head over to Ryan Family Amusements.
Their arcade is packed with classic and modern games that appeal to every generation. Kids can collect tickets for prizes while parents rediscover their favorite arcade games from years ago. It’s the perfect evening activity after a day at the beach.
End the Day with Ice Cream
Vacation simply isn’t complete without ice cream.
Downtown Oak Bluffs has two longtime favorites:
Whether you’re in the mood for a classic cone, a sundae, or one of Ben & Bill’s famous homemade flavors, everyone can find something to enjoy. Grab your treats and stroll through the harbor or relax in Ocean Park while watching the sunset.
Finish the Night Around the Fire
Back at the Oak Bluffs Inn, many evenings end around our backyard fire pit.
We love gathering guests together to roast marshmallows, share stories from the day’s adventures, and enjoy a relaxing Vineyard evening under the stars. It’s often where kids make new friends and parents discover that some of the best vacation memories happen after the day’s activities are over.
The Best Family Vacation Is One Where Everyone Has Fun
Downtown Oak Bluffs has a special way of bringing out the kid in everyone. Whether you’re catching the brass ring on the Flying Horses, flying a kite over Ocean Park, winning prizes at the arcade, or sharing ice cream before heading back to the Inn for a campfire, these simple traditions create memories that last a lifetime.
At the Oak Bluffs Inn, you’re just a short walk from all of it—and we’re always happy to point you toward our favorite family activities
