Coastal view of Rockport, Massachusetts.

The Best Small Town In Massachusetts For A 3-Day Weekend

When people consider locations to choose for a three-day weekend, they might take factors such as whether the accommodation will be welcoming and comfortable, whether there will be high-quality restaurants, a walkable downtown area loaded with shopping and cultural opportunities, and access to the outdoors into account. Finding a destination that brings all of these elements together within a short trip can be challenging. Perched on Cape Ann, Rockport is known for its working harbor, artist studios, and the iconic Bearskin Neck, a narrow peninsula lined with galleries, shops, and ocean views that define the town’s seaside character. This village in Massachusetts, located just 40 miles north of Boston, offers all of this and more. This article takes a closer look at Rockport to see if it is the best small town in Massachusetts for a three-day weekend.

Historic Hotels

Rockport, Massachusetts.
Rockport, Massachusetts.

Rockport is known for its gracious hospitality, which is embodied in hotels like Emerson Inn by the Sea, a boutique hotel with over 150 years of history. The inn is accommodating to all types of guests, whether single travelers or families. It offers ocean view rooms featuring luxurious spa tubs and private balconies with views of the Atlantic Ocean. The inn is renowned for its friendly, helpful, and attentive staff, as well as its numerous amenities, including a seasonal heated outdoor pool, several lounge areas, a historic parlor bar, and complimentary breakfast. The inn’s convenient location in Pigeon Cove grants guests access to walking paths, beaches, and activities like whale watching.

The Rockport House is a restored 1890s Victorian-style manor located just a five-minute walk from downtown Rockport. It is a small boutique hotel with 18 rooms, each uniquely decorated in a way that pays homage to Rockport’s artistic heritage. There are various accommodation types spread across three buildings on the property, including rooms, suites, studios, and a private cottage.

Seaside Spots

Street view in Rockport, Massachusetts.
The Pewter Shop in downtown Rockport, Massachusetts. Image credit: Micha Weber via Shutterstock.com

My Place by the Sea is an award-winning restaurant that specializes in New American cuisine, with a distinct flair for fresh, locally sourced seafood. It is located on the tip of the historic Bearskin Neck in downtown Rockport and features multiple-level seating areas, both indoors and outdoors, for guests to enjoy food, drink, and views of the New England coast.

Floating Lotus is a boutique offering a wide selection of handmade and fair-trade items, including clothing, jewelry, textiles, wood carvings, and musical instruments. They promote cultural diversity, working with both artists from Southeast Asia and regional artists from New England. Before you leave, visit the Pewter Shop for some gifts. This business was established in 1935, making it the oldest gift shop in Rockport. They offer high-quality pewter products from their own workshop, as well as a range of other items, including bath and body products, jewelry, home goods, and kitchen accessories.

Paper House

View of the Paper House in Rockport, Massachusetts.
View of the Paper House in Rockport, Massachusetts. (Image Credit - Conny Pokorny via Shutterstock.com)

The Paper House, as its name suggests, is a house made entirely of paper, along with all the furniture, too. Construction began in 1922 under the direction of a mechanical engineer named Elis F. Stenman, who was responsible for designing the machine that produced paper clips. He began construction of the Paper House with the intention of making it his summer home. Initially, he only planned to use paper as insulation, but the entire house was made using only paper. The house is open seasonally from the second Friday in April to the last Sunday in October, between the hours of 10 am and 5 pm. The house is outside of town and can sometimes be missed. After heading towards Pigeon Cove, turn left onto Curtis Street, then right onto Pigeon Hill.

Coastal Playground

Fishing boat harbor at Rockport, Massachusetts.
Fishing boat harbor at Rockport, Massachusetts.

Sitting along the coast, there is also no shortage of outdoor fun to be had in Rockport. Halibut Point State Park is open year-round for day use only, between sunrise and sunset. Historically, the park has been a site for a granite quarry and has seen military structures erected on it. Today, visitors to the park can hike, explore tidepools, picnic, fish, and observe wildlife. The park hosts numerous events throughout the year, including quarry tours and granite demonstrations every Saturday from Memorial Day weekend to Columbus Day weekend, guided birding walks, and talks about the park’s World War II history. The park offers spectacular views, especially on clear days when visitors can see Mount Agamenticus, located 40 miles away in Maine, and the Isles of Shoals, situated off the coast of New Hampshire.

Another great option is Millbrook Meadow, a four-acre green space in downtown Rockport. Nearly half of the park is occupied by Mill Pond, which is teeming with aquatic plants, turtles, eels, ducks, birds, otters, beavers, and fish. The other half of the park comprises the Meadow, a large, open area accessible year-round, which serves as the site of many seasonal fairs and festivals. The park is across the road from Front Beach and is accessible from Beach Street.

Three Days In Historic Rockport

Street view in Rockport, Massachusetts.
Street view in Rockport, Massachusetts.

Rockport offers a refreshing blend of coastal scenery, artistic character, and small-town charm, making it an ideal place to slow down and enjoy a long weekend at a relaxed pace. It features historic hotels that have been modernized with comfortable amenities, excellent dining options, a vibrant art scene, unique historical landmarks, and great access to the outdoors. This is the best small town in Massachusetts for a three-day weekend.

Share
  1. Home
  2. Places
  3. Cities
  4. The Best Small Town In Massachusetts For A 3-Day Weekend

More in Places