Massachusetts has no shortage of captivating coastal towns, and fall is one of the best times to visit them. As the weather cools and the leaves brown, you’ll experience the ideal weather for relaxed outdoor exploration or hours spent in museums and restaurants.
If you’re wondering which cool coastal Massachusetts towns to visit this fall, we’ve created the below guide including everything from America’s oldest seaport to the site of the first pilgrim settlement. Many of these towns form part of our Day Trips from Boston, making them easily accessible for visitors and locals using the Commuter Railway system.
Let’s dive in!
Gloucester: America’s Oldest Seaport
Just an hour’s train ride north of Boston, Gloucester is one of the most historic cities in the United States. Founded in 1623, it is America’s oldest seaport and the birthplace of the country’s fishing industry. It’s also the home of the Rocky Neck Art Colony, the oldest working art colony in America. Located on the Cape Ann peninsula, Gloucester encapsulates eclectic coastal living in Massachusetts.
Gloucester is a top destination for whale watching, with the Stellwagen Bank National Marine Sanctuary just a boat ride away. Beaches, lighthouses, and fresh seafood restaurants make Gloucester an unmissable day trip. One of its most notable attractions is the Hammond Castle Museum which was first built in the 1920s and now serves as a leading STEM museum, which you can visit on our Hammond Castle Tour from Boston!
Rockport: Home of the Most Painted Building in America
North of Gloucester is another cool coastal town — Rockport. With its coastal scenery and quirky attractions, Rockport is certainly one for the bucket list. The town is most well-known for its iconic red fishing shack, known as Motif #1. First built in 1884, it’s served as the subject for countless artworks and has been given the title of “most painted building in America”.
For even more intriguing buildings, make a stop at the Paper House Museum. This house was built entirely out of paper, including all of the furniture! However, a favorite among visitors and locals is the Halibut Point State Park. Located on a stretch of rocky coastline, it’s the ideal place to go hiking, picnicking, fishing, and bird-watching. As a property of the Trustees of Reservations, it’s also one of our options for Best Boston Day Trips to the Trustees’ Properties.
Plymouth: Where the Pilgrims Arrived
About an hour’s train ride south of Boston, Plymouth is known as “America’s Hometown”. In 1620, the English pilgrims arrived on the coast and established the colony of Plymouth. At Plymouth Rock, you can view the original rock said to have been the stepping stone for pilgrims disembarking their ship.
For a deep dive into history, visit the Plimoth Patuxet Museums which recreates the original Pilgrim colony and brings the 17th century to life. If you want to keep exploring on foot, our Guided Plymouth Walking Tour takes you through the town and includes a scavenger hunt! And just in time for fall, our Haunted History Guided Walking Tour of Plymouth shows you the spooky side of the coastal town.
Sandwich: Oldest Town in Cape Cod
Established in 1637, Sandwich is the oldest town in Cape Cod. Approximately 2.5 hours south of Boston, this town is one of the first you’ll see upon entering the peninsula. While it has a lengthy history, it’s most well-known for its glass. Sandwich was famed for its Victorian-era glass, some of which you can now see at the Sandwich Glass Museum.
Of course, Sandwich and Cape Cod are also renowned for their natural beauty. Sandy Neck Beach offers one of the best beaches in the area, while further inland more adventures await. Join our Cape Cod Kayak Tour at Lawrence Pond in Sandwich for a blissful day spent on the water, where you’ll get to learn more about the wildlife and local area. Pack a picnic lunch to enjoy beside the lake after your tour!
Ipswich: The Birthplace of American Independence
If you want to escape the hustle and bustle of the city, take the 50-minute train journey from Boston to the coastal town of Ipswich. Known as the “Birthplace of American Independence”, Ipswich played an important role in opposing taxes imposed by the British in 1687, leading to the revolution in 1689.
Today, the town is renowned for its delicious clams, the four-mile-long Crane Beach, and historic attractions. The most notable of these is the Crane Estate, spanning over 2,000 acres. During our Castle Hill on the Crane Estate Day Trip, you’ll be transported to 1929 as you explore the Great House and beautifully manicured grounds. If you’re looking for a more active time out, you can also join our Kayaking Trip on Castle Neck River on the estate to kayak in The Great Marsh and spot the wildlife.
Provincetown: A Hub of Artistry
Right at the tip of Cape Cod, Provincetown is known for its artistic culture and vibrant LGBTQ+ community. Also known as P-Town, Provincetown has attracted artists and creatives to its shores for over 100 years, a legacy you can experience through its myriad art galleries and theater performances. Provincetown is also a favorite destination among the LGBTQ+ community thanks to its welcoming atmosphere and numerous events and festivals.
With freedom and expression underpinning this spirited town, you’ll be guaranteed an energetic visit. But with plenty of expansive beaches and hiking trails to explore, Provincetown also offers natural abundance and tranquility.
New Bedford: A Hidden Gem
New Bedford is one of Massachusetts’ up-and-coming coastal towns, with plenty of museums, galleries, cafes, and historic attractions. The town played a prominent role in the Golden Age of Whaling, which you can learn more about at the New Bedford Whaling Museum. Not to be missed is the Seamen’s Bethel, which is said to have inspired parts of Herman Melville’s Moby Dick.
New Bedford is also considered one of the most artistic cities in America. You can admire public art along the Seaport Art Walk or check out the works of local creatives at the New Bedford Art Museum. This coastal town makes for the perfect day trip for culture vultures and history buffs!
Discover More Outside Boston with Keolis massAdventures
These are just some of the cool coastal Massachusetts towns to visit this fall, but more await! If you’re eager to explore more outside Boston, including more inland attractions, browse our full range of Day Trips Near Boston. And if you have any questions for us about tours, don’t hesitate to get in touch!
