Rockport, Massachusetts

8 Picturesque Small Towns Just A Short Drive From Boston

Boston is the epitome of seafaring attractions, both historical and modern. It is known for its waterfront galore of restaurants, fishing piers, and dreamy strolls along the boardwalk with longing looks into the deepest blue and exchanging nods with lighthouses as if in mutual understanding. A generous sprinkling of picturesque towns around Boston within an hour's drive shines brightly with quaint scapes, illuminating the best of the Bay State of Massachusetts. This incredibly-picturesque selection of secret gems and nation-known towns is bound to be the next best weekend getaway in a quintessential atmosphere. 

Concord

Concord Massachusetts.
Tourists kayaking on the Concord River at Minute Man National Historic Park in Concord, Massachusetts.

Concord is a vibrant town with 17,000-some residents and myriad attractions for all tastes, just 45 minutes out of Boston. It preserves a quaint charm with stellar parklands and historical streets from centuries ago as the site of the significant Battle of Lexington and Concord in the American Revolutionary War. The town's natural beauty is elevated by the Walden Pond for summertime recreation and the Minute Man National Historical Park, perfect for year-round discovery hikes. 

Concord boasts one of the best locales-meets New England beauty, at the convergence of Sudbury, Assabet, and Concord Rivers through an attractive town center full of greenery. Various family-oriented landmarks await through the serene Walden Pond State Reservation, an array of local cafes and bakeries, boutiques, and bookshops.

Duxbury

Duxbury, Massachusetts
Aerial view of Duxbury, Massachusetts.

The sweet town, only 34 miles south of Boston, is home to just over 15,000 residents. It is most famous for the Duxbury Beach Park and historic homes-galore, among other big-time attractions. The beautiful park is a summertime recreation destination, with perfectly strollable trails year-round for natural sights and serene relaxation by the water at low tide. 

The Island Creek oyster farm offers wonderful boat excursions to learn about the oyster industry that one can savor after in town. The haunted tavern Island Creek Oyster Bar serves oysters from the oyster farm caught right on Duxbury Bay for the freshest seafood feast of a lifetime. 

Gloucester

Gloucester, Cape Ann, Massachusetts
Wingaersheek Beach aerial view in Gloucester, Cape Ann, Massachusetts.

The brilliant town on the Cape Ann waterfront is a 40-minute drive go-to for Bostonians when vacation time is limited, but vitamin D need prevails. The sunny locale with many beaches is perfect for a summertime weekend trip with exquisite stretches of sand to bask under the beautiful weather. There's a complementing seafood restaurant scene with a significant variety of tasty, freshly-caught options on the menu, from fish to lobster and other sea treasures.

The vast bodies of water and variety of coastlines summon a big fishing culture, with plenty of space for waterside recreation. There's Niles Beach, Half Moon Beach, and Wingaersheek Beach for boating, while Good Harbor Beach is best for swimming. Gloucester contains the oldest harbor in the US, with tons of historical landmarks and charming lighthouses like the impressive Eastern Point Lighthouse from 1832. Honeymooners and families love touring the medieval Hammond Castle Museum, while Cape Ann Museum boasts nautical charms from the past. 

Great Barrington

Great Barrington, massachusetts
Railroad street lined with traditional brick buildings and colourful shops and restaurants in Great Barrington, Massachusetts. Editorial credit: Albert Pego / Shutterstock.com

Great Barrington is home to 7,100 proud residents living in one of the top 20 best small towns in the US, according to the Smithsonian magazine in 2012. The town has come a long way since then, adapting to increasing popularity to become "freakishly perfect." The mountainous appeal attracts sight-seekers, with highland trails seeing hikers and skiers switch according to season.

Hippies and artists love to peruse the compact center of the quintessential Massachusetts town on a weekend getaway from nearby Boston. Food lovers come for the galore of eateries along the picturesque Railroad Street for varied grub oversights. There are tons of historical sites dating back to Colonial times, while Guthrie Center is dedicated to folk music and native son, singer-songwriter Arlo Guthrie.

Ipswich

Ipswich
Ipswich Bridge over Ipswich River in Central Street in spring at town center of Ipswich, Massachusetts.

The whimsically-named town is one of the state's best-kept secrets offering plentiful natural beauty for solitude-seekers, with an especially-welcoming vibe from locals. Those after New England traditions and charm come to Ipswich, the bonafide for both, just 45 minutes out of Boston. It is hard to outshine coastal locales, but the Orwell River, running through town, and one of the state's best, Crane Beach, offer serenity that the masses still need to learn about.

There's all the space for relaxation, clear views, and vast waters for peaceful swimming and relaxation in nature, even during summertime. For natural sights, there is easy access to parklands like the Daniel Boone Park and Julia Bird Reservation, and even a wolf foundation. Other family attractions include Castle Hill on the Crane Estate and restaurants galore along the main street, with pubs and breweries to savor precious vacation time in good company.

Newburyport

Newburyport
View of the Bridge and Rings Island marina on the Merrimack River from Bridge Street (US Route 1) in Newburyport on a sunny fall day. Editorial credit: Sergey and Marina Pyataev / Shutterstock.com

With an adorable name like that, the town cannot help being one of the state's cutest. The coastal gem with easy access from Boston in 50 minutes is incredibly-picturesque and deeply historical. Newburyport dates back to the Revolutionary War, following which it became an important stop on the Underground Railroad and gained touristic popularity. The town flaunts an idyllic mix of contemporary and old-fashioned attractions wrapped in New England charm.

There are vibrant pursuits like whale watching, nautical strolls along the lovely boardwalk, and ice cream parlors. The main thoroughfare along the High Street is home to picturesque Federal-style houses, while shopaholics head to the State Street promenade. The town, with about 18,000 residents, boasts an optimal location where Merrimack River meets the sea for summertime recreation, antique shopping, and scenic trails through the Parker River National Wildlife Refuge.

Rockport

Rockport, Massachusetts
The picturesque harbor in Rockport. 

The charming seaside village of Rockport is a real-life postcard with a pronounced New England feel. The enclave along a picturesque scrap of Cape Ann was a 19th-century granite-mining town, turned into a reputable tourist destination and home to some 7,500 residents. The aptly-named town boasts natural scenery of stone beaches, wildly-unique surroundings, and the famous red fishing shacks. These often appear on travel magazine covers, and one can watch artists capture the scenery on easels during a weekend-trip getaway from their Boston lofts.

The tiny peninsula of Bearskin Neck is perfect for a family vacation and a must-stop on a road trip. There are tons of cute touristy attractions like art galleries and gift shops dotted around the harbor amidst plenty of amenities and some of the region's top restaurants and bars. The active thoroughly enjoy hiking waterside trails through the idyllic Halibut Point State with picnicking areas, tidal pools, and lookout points that extend well into New Hampshire and Maine. 

Salem

Aerial view of Salem historic city center including Salem Witch Museum and Andrew Safford House in city of Salem, Massachusetts MA, USA.
Aerial view of Salem's historic city center including Salem Witch Museum and Andrew Safford House in city of Salem, Massachusetts.

The notorious Salem, just 15 miles from Boston, is known for 1692 witch trials with over 200 accused of craft. Today, the town pleads guilty for spellbinding visitors on anytime getaway with second-to-none natural vistas. The stunning Riverfront Park feels eons away from the capital, and cruises to watch Salem float away into the distance. The harbor location along the northern Massachusetts coast is rumored to charm people on wistful strolls, while the Essex Street Pedestrian Mall can make money disappear. The Peabody Essex Museum tells intriguing tales through artifacts surrounding the town's fascinating past.

Salem is also family-friendly, with various pursuits to engage the little ones and let parents enjoy time off and unwind from work. There is a galore of fun sights and activities on Halloween, and eye-catching attractions like the Riverfront Carousel and The Gilbert House Children's Museum will hold the interest of the entire clan. Nature fans enjoy the bountiful greenscape at the Minto-Brown Island Park, Bush Park and Conservatory, and the magnificent Willamette River. The Christo's Café and Ticket to Play Board Game Café are fancy and unique dining options, while dads love the eerie vibe at the Fitzgerald Public House inspired by the famed author.

These attractive towns drip with nautical charm veiled in New England traditions and beautiful nature for an idyllic weekend getaway from Boston. One will leave feeling refreshed and with a belly full of freshly-caught seafood for a true state of relaxation to delve back into work clear-headed.

Share
  1. Home
  2. Places
  3. Cities
  4. 8 Picturesque Small Towns Just A Short Drive From Boston

More in Places