A must do for new comers to the Island is enjoying a stroll through Trinity Park to see the "Gingerbread Houses". The area is a popular tourist attraction and offers a glimpse into the island's rich history. The cottages are a unique and iconic feature of Martha's Vineyard. They are a part of the Martha's Vineyard Camp Meeting Association (MVCMA), a historic community founded in the 19th century as a Methodist campground. The cottages are known for their vibrant colors, intricate gingerbread trim, and quaint Victorian-style architecture. We highly recommend grabbing a coffee at Toccopuro in downtown Oak Bluffs and head up to Tabernacle Ave, path that leads directly to the grounds.

No stop to downtown Edgartown is complete without visiting the picturesque Edgartown Lighthouse. The area around the lighthouse offers beautiful views of the harbor and is a great spot for pictures. We recommend parking on the street near the beautiful Harbor View Hotel and make your way down a short trail walk to the lighthouse.

The beautiful clay cliffs in Aquinnah are not to be missed, this amazing geological formation is one of the most visited tourist spots on the island.

Two easy-to-explore trails provide access to the upland surrounding the cliffs and lead down to the shore, where you can walk miles of coastline beneath the cliffs.

There are a few seasonal shops located at the top of cliffs near the parking area along with views of the Gay Head Lighthouse.

Martha's Vineyard has 6 major towns to explore, each own has its own individual uniqueness making it hard to recommend just one!

For Walkable Shopping, Coffees, and Restaurants:

Edgartown: Known for its elegant charm, cobblestone streets, and historic architecture, Edgartown has a variety of boutique shops, coffee spots, and fine dining restaurants. The harbor area is particularly scenic. The downtown may look particularly familiar for any Jaws fans!

Oak Bluffs: Famous for its colorful gingerbread cottages in the MVCMA campground, Oak Bluffs has a lively atmosphere with many shops, cafes, and restaurants. The Flying Horses Carousel is a nostalgic attraction.

Vineyard Haven: Serving as the primary port of entry, Vineyard Haven offers a mix of shops, galleries, and eateries. Here you can eat at the famous Black Dog Tavern and purchase a Black Dog T-shirt for the Monica in your life.

For Scenic Nature Views, Maritime Exploration, and Quieter Spots:

Chilmark/Menemsha: Known for its rural charm, Chilmark offers rolling farmland and the serene Menemsha Hills. Menemsha, a fishing village, provides beautiful sunset views over the harbor. We love popping in to Larsen's Fish Market to check out the daily catch and sample some freshly made Clam Chowder.

Aquinnah: Formerly known as Gay Head, Aquinnah is home to the Wampanoag Tribe and the iconic Gay Head Cliffs. It offers a quieter, more rural atmosphere with a focus on Native American culture.

West Tisbury: Celebrating its agricultural heritage, West Tisbury is known for the Martha's Vineyard Agricultural Fair. The Polly Hill Arboretum is a botanical attraction in the area.