The Meetinghouse is a community center for the arts. The goal is to bring the community together to support and encourage literary, visual and performing arts. The center offers free afternoon programs for young children as well as evening and weekend workshops for adults and teenagers. In addition, The Featherstone features concerts, gallery shows, art and history exhibits, lectures and performances.

In the 1800s, religious camps were popular on the island. As popularity increased, this open-air wrought iron structure was built, which is believed to be the largest of its kind in the US. With seating for 3,000 people and exquisite woodworking and stained glass, it is truly a magnificent sight. In 1979, its centennial year, it was added to the National Register of Historic Places. The Tabernacle is used today for concerts, Sunday church services, community sing-alongs and special ceremonies.

The historic Union Chapel, with its unique octagonal cupola, was built in 1870 by the architect Samuel Freeman Pratt. The quaint and lovely building is located in the center of Oak Bluffs. The building is particularly known for having wonderful acoustics, which has made it one of the most popular spots on the island for weddings, performing arts, concerts and festivals.

Since the time it was constructed in 2012, Dreamland MV has firmly established itself as one of the best event venues in the town of Oak Bluffs. This 5300 square foot (492.386 square meter) space is just as popular as a concert venue as it is for private functions, and has many excellent facilities on offer. Close to the ferry docks, this venue can accommodate a maximum of 500 people.