6 Best Massachusetts Towns For A Weekend Trip

The weather is still frosty, but that shouldn’t stop you from daydreaming about warmer days. Once the temperatures finally climb, you’ll want to be ready to pack your bags for a weekend away! If you need a little inspiration, the following six Massachusetts towns are perfect for your radar, whether you’re craving Marblehead’s harbor strolls or a gallery-filled afternoon in Provincetown. Whale watching tours, botanical gardens, castles, harborfront seafood restaurants, and museums housing famous artist works are a few of the memorable attractions that await in the towns below.

Marblehead

There is no need to travel far this year for your weekend away, and Marblehead is the perfect example. This town is just 17 miles north of Boston and is largely known for its fishing industry and history. Travelers can grab some incredibly fresh seafood at The Landing Restaurant, located right on Marblehead Harbor, which serves craft cocktails, New England clam chowder, crispy haddock, swordfish, salmon, and many other specialties. Once your belly is full, head over to Chandler Hovey Park for a stroll or swim, a 3.74-acre park that overlooks the mouth of the harbor.

In the summer, you can explore some of Marblehead’s history at the Jeremiah Lee Mansion & Garden, a 1768 Georgian home that was built for the period’s wealthiest merchant in colonial Massachusetts. Many of the town’s inns are historic as well, like the Harbor Light Inn, which features 18th-century architecture and fine chandeliers, hand-carvings, brasswork, paintings, intricate furnishings, and more.

Northampton

Nicknamed “Paradise City,” Northampton is filled with gardens, museums, and galleries that make it feel like something out of a movie set. The Botanic Garden of Smith College is a great example: a massive green space with a 127-acre arboretum, a 12,000-square-foot conservatory, and 6 acres of outdoor-managed gardens to explore. The Smith College Museum of Art is another beautiful attraction, featuring an extensive collection of everything from Greek vases to modern video pieces. If you are looking to browse even more art afterward, you can also stop by the R. Michelson Galleries, which stands as Western Massachusetts’ largest commercial art gallery. Finish off the day by checking into Hotel Northampton, built in 1927, with 106 elegant rooms.

Newburyport

Established as its own town in 1764, Newburyport has a proud maritime heritage and history that visitors can comfortably explore in one weekend. The Custom House Maritime Museum harbors a large portion of this history, exhibiting a collection of maritime art, shipwreck displays, model clipper ships, and more. Don’t miss out on the chance to tour the Plum Island Lighthouse either, which was the 13th lighthouse to be built in the country. Guided tours are typically available on select dates between May and September. Heading outdoors, you will find scenic attractions like ​​Maudslay State Park, which is filled with 19th-century gardens, towering pines, and rolling meadows. The Essex Street Inn is a cozy place to spend the night, a 19th-century property that has king and queen bedrooms and suites.

Provincetown

As one of the oldest continuous art colonies in the country, Provincetown should be on your weekend radar if you love art. The dedicated art community has created prized institutions like the Provincetown Art Association and Museum (PAAM), which holds over 5,000 pieces of art. You will also find many galleries along Commercial Street, including the Bowersock Fine Art Gallery, which has been showcasing art for over two decades. Once the weather is warmer, you can enjoy a day on one of the area’s beaches, such as Herring Cove Beach, which is part of the Cape Cod National Seashore, popular for its gentler waves and slightly warmer temperatures. You can wrap up your day with even more art at the White Porch Inn, an 1840s-era hotel that has been renovated and furnished with contemporary art throughout.

Stockbridge

If you couldn’t get enough of Provincetown’s art, you will definitely want to plan a follow-up weekend trip to Stockbridge! This little town is home to the Norman Rockwell Museum, which was founded in 1969 with the help of Rockwell himself. You will find the largest collection of Rockwell’s work in the world here, including nearly 1,000 paintings and drawings. In addition to all of the art, the museum also houses over 100,000 items from Rockwell’s life, including letters, photographs, business documents, fan letters, and more.

While in town, you won’t want to miss a visit to the Berkshire Botanical Garden, which is one of the oldest gardens of its kind in New England and encompasses over 24 acres. If you are looking for a lovely way to conclude the day, consider making reservations at the Red Lion Inn, which has been welcoming travelers since 1773, composed of both the Main Inn and additional village houses scattered around the property.

Gloucester

While you will find all the standard beach town fun in Gloucester, the city also has some more unique attractions. The first is the Hammond Castle Museum, a medieval-style castle that was created by inventor John Hays Hammond Jr., today displaying antiques and 20th-century technology exhibits. You may also enjoy signing up for a whale-watching tour with 7 Seas Whale Watch, which has been operating in the community since 1983. Humpback, finback, minke, and pilot whales are just a few of the possible species you might spot! You can also stay near the action all weekend long by lodging at the Harborview Inn, which is located near numerous shops, restaurants, galleries, museums, and more. Many rooms have a harbor view as well!

A Memorable Trip Within Your Own State

It is important to remember that a vacation can come in all shapes and forms. While planning a two-week-long, international trip is always exciting, you can often have just as much fun on a short weekend away within your very own state. And these six towns are an excellent reminder of such, offering all kinds of itineraries focused on art, maritime history, beach recreation, and more! All you have to do is pick the town that spoke the most to you and get ready to have a memorable weekend.