Top 8 Massachusetts Destinations for a Perfect Long Weekend

Casey Halston

Published: February 8, 2026 7:48 PM ET

Massachusetts is a region steeped in history and natural beauty, boasting a variety of destinations for a perfect long weekend. Here are eight of the top locations that offer unique experiences for visitors looking to explore this beautiful New England state.

Top 8 Massachusetts Destinations for a Perfect Long Weekend

1. Williamstown

Located in the northwestern corner of Massachusetts, Williamstown is known as “The Village Beautiful.” This scenic town offers access to state parks and preserves, ideal for hiking and wildlife observation.

Attractions: The Clark Art Institute and the Williams College Museum of Art feature a rich collection of art from various periods.
Accommodations: Stay at The Williams Inn for a charming experience in the heart of town.

2. Lenox

Lenox, nestled in the Berkshires, is a cultural hub and home to key attractions like the Norman Rockwell Museum and Tanglewood music festival.

Recreation: Visitors can enjoy the Pleasant Valley Wildlife Sanctuary for hiking and relaxation.
Spa Experience: Miraval Berkshires offers a luxurious retreat with wellness treatments and elegant dining options.

3. Great Barrington

This mountain village serves as a base for winter sports enthusiasts, with two major ski resorts nearby.

Activities: Mount Washington State Forest features extensive trails for hiking, biking, and cross-country skiing.
Lodging: Prospect Berkshires provides comfortable cabins and lakeside dining for a cozy stay.

4. Northampton

Known as “Paradise City,” Northampton offers a vibrant arts scene and numerous cultural sites.

Cultural Sites: Smith College Museum of Art and the Calvin Coolidge Presidential Library attract many visitors.
Outdoor Activities: Enjoy the tranquility of Mineral Hills Conservation Area, which has several hiking trails.

5. Sturbridge

Steeped in history, Sturbridge is home to the living museum Old Sturbridge Village, showcasing early 19th-century life.

Historical Experience: Tantiusques offers insights into indigenous mining activities with remnants of historical operations.
Outdoor Fun: Explore Wells State Park’s trails and engage in various recreational activities.

6. Salem

Salem, famous for its witch trials, attracts visitors year-round for its educational and historical offerings.

Museums: The Salem Witch Museum and Peabody Essex Museum are must-visit sites for history buffs.
Accommodations: The Merchant Salem Hotel features modern amenities in a historic setting.

7. Provincetown

Cape Cod’s artistic hotspot, Provincetown, is known for its stunning beaches and vibrant arts scene.

Attractions: The Provincetown Art Association and the Cape Cod National Seashore are highlights for visitors.
Stay: The Ellery Hotel offers stylish accommodations near local galleries and beaches.

8. Nantucket

About 30 miles off the coast of Cape Cod, Nantucket features picturesque landscapes and historic lighthouses.

Nantucket Highlights: Visit the Great Point Coskata-Coatue Wildlife Refuge and Sankaty Head Lighthouse.
For Relaxation: Greydon House serves as a chic accommodation featuring exceptional dining and luxurious amenities.

From the mountains of the Berkshires to the enchanting coastlines of Cape Cod, Massachusetts offers diverse destinations perfect for a long weekend getaway. Each location invites exploration and guarantees memorable experiences for every traveler.