The Best Day Trips in Massachusetts (and the Best Time to Go)

Jan 12

Massachusetts may be small, but it’s filled with diverse destinations perfect for a day trip any time of year. From historic towns to coastal escapes, here are some of the best day trips in Massachusetts—plus when to visit each for the best experience.

1. Salem

Best time to visit: September–October or May–June

Salem is one of the most popular day trips in MA, especially in the fall. October brings peak foliage and spooky-season festivities tied to the city’s witch trial history. For fewer crowds and pleasant weather, late spring is also an ideal time to explore the Salem Witch Museum, Derby Wharf, and downtown shops.

2. Cape Ann (Rockport & Gloucester)

Best time to visit: June–September

Cape Ann shines in the summer months. Rockport and Gloucester offer classic New England coastal charm, fresh seafood, and beautiful beaches. Late June and early September are sweet spots, with warm weather and fewer crowds than peak summer weekends.

3. The Berkshires

Best time to visit: October or July–August

The Berkshires are a year-round destination, but fall foliage in October is especially stunning. Summer is another excellent option, thanks to outdoor concerts, hiking trails, and cultural attractions like Tanglewood and MASS MoCA. This western Massachusetts escape is perfect for nature lovers and art enthusiasts alike.

4. Concord & Lexington

Best time to visit: April–June or September–October

Spring and fall are the best seasons to visit Concord and Lexington. Mild temperatures make it ideal for walking the Battle Road Trail and exploring Minute Man National Historical Park. Autumn also brings beautiful foliage around Walden Pond and other historic sites.

5. Martha’s Vineyard (Day Ferry Trip)

Best time to visit: June or September

While often considered a longer getaway, Martha’s Vineyard makes a memorable Massachusetts day trip in early summer or early fall. June and September offer warm weather, open shops and restaurants, and fewer crowds than July and August.

Plan the Perfect Massachusetts Day Trip

No matter the season, these top day trips in Massachusetts offer history, scenery, and unforgettable experiences—all within a short drive or ferry ride. Pick the right time of year, and your next adventure is closer than you think.

M. Zarella