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Oak Bluffs Harbor | © Ernest McGray, Jr. / Flickr
Oak Bluffs Harbor | © Ernest McGray, Jr. / Flickr

Massachusetts' Best Seaside Towns to Visit

Picture of Ashley Kane
Freelance Writer
Updated: 15 February 2017
Filled with stunning coastal towns, Massachusetts is a great place to visit year-round. While many of these destinations are popular during the summer for swimming and sunbathing on their idyllic beaches, others are just as enjoyable in the off-season, and much less crowded. Choose one of these beautiful seaside towns to relax in and start planning a trip now.

Oak Bluffs, Martha’s Vineyard

Oak Bluffs is a beautiful town on Martha’s Vineyard. Board a ferry to the island from mainland Massachusetts, and enjoy a weekend exploring this summer destination. Take in the scenic views of the harbor and East Chop Light before spending some time wandering around the quaint Wesleyan Grove district, dotted with historic, ornate gingerbread cottages. There are over 300, brightly colored cottages to look at, and all were originally part of the first summer religious camp in the United States. Today, you can rent the cottages, take walking tours, or participate in spiritual services there as part of the Martha’s Vineyard Camp Meeting Association.

Oak Bluffs, MA, USA

Gingerbread Cottages | © Wikimedia Commons

Gingerbread Cottages | © Le Grand Cricri


Gloucester is a charming coastal town on the North Shore of Massachusetts. Take a tour through the stunning seaside Hammond Castle and learn about the famous Gloucester Fisherman’s Memorial. Those looking for a beach day will love the Good Harbor sandy beach, surrounded by marshes and dunes.

Gloucester, MA, USA


Located at the very end of Cape CodProvincetown is a top tourist destination in the summer. Enjoy the downtown shops, spend the day at Race Point Beach, and chow down on fresh seafood at one of the many restaurants in town. The Lobster Pot is known for their delicious, huge lobster rolls, and Provincetown Portuguese Bakery makes delicious breakfasts and desserts.

Provincetown, MA, USA

Lobster Roll from the Lobster Pot in Provincetown | © m01229

Lobster Roll from the Lobster Pot in Provincetown | © m01229 / Flickr


Rockport is a picturesque seaport village, located at the tip of the Cape Ann peninsula. Take pictures of “Motif #1” (the scene below), dubbed so in 1945 for the view’s popularity, before wandering around the art galleries and shops. Halibut Point State Park is nearby if you’d like to get closer to the ocean. Walk down a one-mile (1.6-kilometer) flat path to reach a vista overlooking the sea, where you’ll be able to see the coasts of New Hampshire and Maine.

Rockport, MA, USA

Rockport | © Eric Wittman / Flickr

Rockport | © Eric Wittman / Flickr


Like Martha’s Vineyard, Nantucket is another island that is only one ferry away from the mainland. The island was a 19th-century whaling hub, and visitors can stop by the Nantucket Whaling Museum to learn more about this historic town. Though smaller than Martha’s Vineyard, there is still plenty for visitors to do: explore boutiques downtown, relax on sandy, dune-backed beaches, and stroll through cobblestone streets past historic steepled churches.

Nantucket, MA, USA


Wellfleet lies halfway between the tip and the elbow of Cape Cod. It features the incredible Marconi Beach, part of the Cape Cod National Seashore, and one of the few drive-in movie theaters left in the state. Be sure to stop by The Beachcomber after a beach day for fresh seafood, drinks, and live music. With something for everyone, Wellfleet also has miles of beautifully paved bike paths as well as whale-watching tours and golf courses.

Wellfleet, MA, USA

Wellfleet Harbor | © Rick Harris / Flickr

Wellfleet Harbor | © Rick Harris / Flickr