Things to do in Oak Bluffs
Discover amazing Oak Bluffs activities and premium in-home experiences.
Oak Bluffs is a vibrant seaside town where charming gingerbread cottages meet sandy shores and azure waters. Known for its spirited atmosphere, lively harbor, and historic Flying Horses Carousel—the oldest in the nation—this enchanting destination invites visitors to enjoy leisurely walks along Ocean Park or savor fresh seafood while watching sailboats drift by. Whether you're biking through scenic paths or indulging in sweet treats from local bakeries, Oak Bluffs offers an idyllic slice of coastal life that captivates at every turn.
Popular Activities in Oak Bluffs
Martha's Vineyard Island Tour & Menemsha Feast
Customize your island tour with a Menemsha seafood picnic and complimentary wine
Martha's Vineyard Sunset Tour with Dinner
Watch the sun set over Menemsha Beach aboard a comfy shuttle with dinner options and local commentary
Martha's Vineyard Tour of 6 Towns in 3 Hours
Discover all six Martha's Vineyard towns in a small-group guided bus tour.
Parasailing in Oak Bluffs: 600 Foot Flight
Soar 600 feet above the water with a dry deck takeoff and landing
Jet Ski Rental in Oak Bluffs, Martha's Vineyard
Ride a Yamaha WaveRunner for an exhilarating hour on Martha's Vineyard waters.
Martha's Vineyard Private Tour: Cliffs & Villages
Discover Martha’s Vineyard’s iconic cliffs and villages on a flexible private tour.
Martha's Vineyard Kayak Rentals: 4 to 7 Days
Explore Martha's Vineyard waterways for up to a week with fully equipped single or tandem kayaks.
Oak Bluffs Family Beach Party with Setup
Enjoy a carefree day on the beach while we handle all setup, gear, and cleanup
High-Performance Road Bike Rental in Edgartown
Rent top-tier carbon or aluminum road bikes to explore the island.
Martha's Vineyard Private Tour: Towns & Beaches
Customize a 4-hour private drive to historic towns, lighthouses, beaches, and scenic cliffs with a local guide
Edgartown Private Sunset Cruise with Cocktails
Savor sunset views around Cape Cod and Martha's Vineyard on an exclusive evening cruise for your group
Nantucket Sailboat Rental: 2-Hour Rhodes 19
Enjoy a two-hour self-guided sail aboard a stable Rhodes 19 from Jetties Sailing Center
Learn to Sail with Personal Coach in Nantucket
Build confidence on the water with a dedicated instructor and custom coaching for up to three sailors
Nantucket Harbor Kayak & Paddleboard Rentals
Glide across Nantucket Harbor on your choice of kayak or paddleboard
Private 1.5Hr Kids Sailing Lesson in Nantucket
Learn essential sailing skills in a personalized 1.5-hour session for kids aged 5–12
Learn to Fly Above Water on an eFoil in Nantucket
Learn to ride an electric hydrofoil with expert instruction in Nantucket
Captain Your Own 21ft Whaler Around Nantucket
Cruise Nantucket Harbor with up to 8 friends on a stable, powerful 200hp center-console.
Cape Cod Bay Fishing Charter with Expert Crew
Cast lines in Cape Cod Bay with experienced crew and soak in scenic coastal views
In-Home Experiences
Electric Beach Cruiser Rental in Edgartown
Cover more ground effortlessly with pedal-assist power on colorful cruisers.
Explore the Charm of Oak Bluffs
Oak Bluffs is a vibrant seaside town known for its colorful gingerbread cottages, lively harbor, and rich history. As you stroll through the streets, you'll be captivated by the Victorian architecture that gives this place its unique charm. A visit to Oak Bluffs wouldn't be complete without experiencing the Flying Horses Carousel—the oldest operating platform carousel in America. It's a delightful ride back in time that's perfect for all ages.
For those who love nature, head over to Ocean Park where expansive lawns meet stunning ocean views. This is an ideal spot for picnicking or simply soaking up some sun while enjoying live music during summer concerts. Don't miss out on exploring nearby East Chop Lighthouse; it's one of Martha's Vineyard’s iconic landmarks offering panoramic vistas that are sure to inspire awe.
Whether you're savoring fresh seafood at local eateries or cycling along scenic trails like State Beach Road, Oak Bluffs offers endless opportunities for discovery and relaxation. The island vibe here is both welcoming and invigorating—a refreshing alternative to busier destinations nearby. With its blend of cultural richness and natural beauty, Oak Bluffs promises memorable experiences around every corner.