Part of our Massachusetts guide.
Places and guides from our Massachusetts coverage, gathered into one page.
Related travel guides: Beaches In Massachusetts, Secrets Of Monomoy Island In Massachusetts, Hidden Cape and Forest Gems In Massachusetts, Historic Fishing Traditions In Massachusetts, 11 Spectacular Beaches To Visit In Barnstable Town, Massachusetts, and Hidden Beaches Of Massachusetts.
What Should I Do On A Day Trip To Cape Cod
Spend a day exploring Cape Cod’s beaches, towns, and coastal trails. The peninsula offers natural beauty, history, and outdoor activities within easy reach of the mainland.
Start by crossing the Sagamore or Bourne Bridge and head to a beach. Cape Cod National Seashore stretches 40 miles from Chatham to Provincetown, with beaches like Coast Guard Beach in Eastham and Race Point in Provincetown. Parking fees at seashore beaches are typically $25 per vehicle from late spring through early fall. For a quieter spot, try Sandy Neck Beach in Barnstable or Mayflower Beach in Dennis.
After the beach, explore a town. Chatham has a historic fish pier where seals gather, and Main Street is lined with shops and galleries. Provincetown, at the tip, offers art galleries, the Pilgrim Monument, and whale-watching cruises that run from April through October (tickets around $55–$70 per adult). Walk or bike a section of the Cape Cod Rail Trail, a 25-mile paved path that runs from Dennis through Wellfleet.
For lunch, stop at a raw bar for oysters or a clam shack for fried clams and lobster rolls. Many towns have farmers’ markets in summer—Wellfleet’s runs Wednesdays from June through September. End your day with a sunset walk on a bay-side beach like Skaket Beach in Orleans, where the tide goes out far enough to walk on sand flats. The Cape’s connection to the Salem witch trials is slim, but nearby Plymouth offers a different colonial history.
Pittsfield, Massachusetts: A Guide To Your Weekend Getaway
Pittsfield in Berkshire County works well for a weekend trip focused on arts, history, and outdoor recreation. The city sits a 2.5-hour drive west of Boston via the Massachusetts Turnpike (I-90) and about 45 minutes from Albany, New York.
Start Saturday at the Berkshire Museum, which holds art, natural history, and a small aquarium (admission $15 adults, $8 children). Then walk to the Colonial Theatre, a restored 1903 performance venue that hosts concerts and plays year-round. For lunch, head to North Street, the main downtown strip, where you’ll find farm-to-table restaurants and casual cafes. In the afternoon, drive 10 minutes to Balance Rock State Park for a short hike among glacial boulders, or 15 minutes to Bousquet Mountain for hiking and mountain biking trails.
Sunday, visit the Hancock Shaker Village, a living-history museum 10 minutes west of Pittsfield (open May–October, $20 adults). It includes original Shaker buildings, farm animals, and demonstrations of crafts and cooking. The nearby Appalachian Trail crosses through the Berkshires; the trailhead at Mount Greylock is a 20-minute drive north. For a relaxed afternoon, explore the Pittsfield State Forest, which offers 11 miles of trails and a swimming beach on Berry Pond.
Dinner options range from Italian at Trattoria Il Panino to contemporary American at The Rooftop at the Hotel on North. The city’s arts scene includes First Fridays Artwalk (May–October) and year-round gallery shows at the Lichtenstein Center for the Arts. Pittsfield sits close to Lenox and Stockbridge, each a 10-minute drive south with additional museums and music venues.
