Oak Bluffs History
We were not surprised when our town was recently rated by Conde Nast as Top 10 Coolest Beach Towns on the eastern seaboard. The town of Oak Bluffs in unique and has something for every one. It is a place that you will discover as you visit and many times people are surprised at the laid-back and welcoming atmosphere.
Oak Bluffs is a diverse, welcoming and lively community with long tradition of embracing visionary visitors for generations.
The town was originally called "Cottage City and is well known for the Victorian gingerbread beach cottages. The cottages are brightly colored and uniquely decorated. It all started with the summer religious meetings of the Methodists in the mid-18th century.
The Methodists met in tents that eventually became small summer cottages with no heat and no water. They had lanterns and they met in the wooded clearing to gather, sing and pray. Our community is proud of our interdenominational and interracial harmony that makes it a beacon for people of similar values.
Historical tours of the Methodist campground, the MV African American heritage trail, and Wampanoag Native American cultural center all provide a richer understanding of the place. The newly opened MV Museum guide you on a rich history and island stories of more than 300 years.
Natural Adventures Await
The island has more than 100 miles+ of bike paths, hiking trails and rolling hills that pass by colonial era farms, stately Whaling Captain houses, stunning clay cliffs, quiet harbors, and working fishing villages. The island has a perfect balance that allows you to be lost in nature or vibrant gatherings in a uniquely diverse community.
There truly is something for everyone and depending on your day you can craft your perfect vacation.
- Gingerbread Victorian Cottages (Oak Bluffs)
- Jumping the Jaws Bridge (Oak Bluffs)
- Whaling Captain Homes (Edgartown)
- MV Museum (Vineyard Haven)
- Beach Bike Ride from Oak Bluffs to Edgartown
- Chappequiddick Island & Cape Pogue Nature Reserve
- Vineyard Artisans Festival & Farmers Market (West Tisbury)
- Lobster on teh Dock & Menemsha Sunset (Menemsha)
- Aquinnah Lighthouse & Cliffs with Wampanoag Cultural Center
- Deep Sea or Harbor Fishing (Oak Bluffs Harbor)
- Paddleboard & Kayaking (Sengegontacket Pond)
- Too many quiet beaches and trails to list...
Whether this is your first visit, or you have been a guest for many seasons, we are here to help. Our staff is on hand and happy to help with any questions or reservations you may need.