Westwood, MA, is a charming suburban town just outside of Boston, known for its close-knit community, excellent schools, and picturesque neighborhoods. Its proximity to major highways like Interstate 95 and Route 128 makes it a convenient base for exploring some of New England’s most popular destinations. Whether you’re looking to escape to the coast, explore historic towns, or enjoy scenic outdoor adventures, Westwood’s location provides easy access to a variety of weekend getaways.
Here’s a guide to the best weekend trips from Westwood MA, highlighting destinations that offer something for everyone.
Westwood’s Climate
- The most pleasant months in Westwood are June, July, and August.
- Four months have comfortable high temperatures ranging from 70-85°F.
- July is the hottest month, with an average high of 82.6°F, making it warmer than most places in Massachusetts.
- January is the snowiest month, with an average of 13.8 inches of snow.
- Significant snowfall occurs during six months of the year.
- July is the most humid month, though humidity levels are milder compared to many other locations.
Weekend Trips from Westwood
Newport, Rhode Island
Distance: 50 miles
Newport, Rhode Island, is a seaside treasure steeped in history and elegance. The town’s famous Gilded Age mansions, such as The Breakers and Marble House, provide a glimpse into America’s opulent past. Visitors can enjoy the scenic Cliff Walk, a 3.5-mile path that combines stunning ocean views with glimpses of historic architecture. For food lovers, Newport boasts various waterfront restaurants serving fresh seafood, including lobster rolls and clam chowder. The town also hosts events like the Newport Jazz Festival and sailing regattas, making it an engaging destination throughout the year.
Cape Cod, Massachusetts
Distance: 60 miles
Cape Cod offers a quintessential New England coastal experience with its sandy beaches, charming villages, and relaxed pace of life. Popular beaches such as Nauset Beach and Mayflower Beach are ideal for swimming, sunbathing, and collecting seashells. Visitors can also explore the Cape Cod Rail Trail, a scenic bike path that winds through picturesque landscapes and quaint towns. The area is home to iconic lighthouses, art galleries, and seafood shacks where you can enjoy fresh lobster and fried clams. For a more immersive experience, consider taking a whale-watching tour or visiting Provincetown, known for its vibrant arts scene.
Portland, Maine
Distance: 85 miles
Portland, Maine, combines small-town charm with urban sophistication, offering a unique coastal getaway. The Old Port district is a must-visit, featuring cobblestone streets, boutique shops, and an array of restaurants known for their fresh seafood. Don’t miss the iconic Portland Head Light, one of the country’s oldest lighthouses, which offers breathtaking ocean views. Portland is also a hub for craft breweries, with popular spots like Allagash Brewing Company offering tours and tastings. The city’s thriving arts scene includes galleries and the Portland Museum of Art, making it a well-rounded destination.
The Berkshires, Massachusetts
Distance: 120 miles
The Berkshires offer a serene escape with rolling hills, artistic attractions, and charming small towns. Tanglewood, the summer home of the Boston Symphony Orchestra, provides world-class music performances in a stunning outdoor setting. For nature enthusiasts, Mount Greylock State Reservation offers hiking trails with sweeping views of the surrounding countryside. The region’s towns, such as Lenox and Stockbridge, are home to farm-to-table dining, boutique shopping, and attractions like the Norman Rockwell Museum. In addition to its cultural offerings, the Berkshires are a haven for wellness retreats, with spas and yoga studios dotting the area.
Mystic, Connecticut
Distance: 70 miles
Mystic, Conn., is a historic coastal village with charm and maritime history. The Mystic Seaport Museum offers a fascinating look at New England’s maritime past, featuring restored ships and interactive exhibits. Families will enjoy the Mystic Aquarium, which is home to beluga whales and other marine life. The town’s downtown area is ideal for strolling, with unique shops, cozy cafes, and the iconic Mystic Pizza. For those who love the water, harbor cruises and paddleboarding are popular activities.
Manchester-by-the-Sea, Massachusetts
Distance: 40 miles
Manchester-by-the-Sea is a picturesque coastal town offering pristine beaches and a laid-back vibe. Singing Beach is a standout attraction, known for its smooth sand and the unique sound it makes underfoot. Kayaking and paddleboarding in the calm waters are popular pastimes for visitors. The town’s quaint downtown is home to boutique shops and local eateries, perfect for exploring after a day by the water. The peaceful atmosphere and natural beauty make Manchester-by-the-Sea an excellent choice for a relaxing weekend trip close to home.
Woodstock, Vermont
Distance: 120 miles
Woodstock, Vt., is a charming New England town known for its historic covered bridges, rolling hills, and friendly community. The Marsh-Billings-Rockefeller National Historical Park offers scenic hiking trails and gardens to explore. Nearby, Billings Farm & Museum provides insight into Vermont’s agricultural heritage. The town’s center has locally owned shops, art galleries, and cozy cafes. Woodstock is especially enchanting in the fall when the vibrant foliage transforms the landscape into a colorful wonderland.
Plymouth, Massachusetts
Distance: 40 miles
Plymouth is a town rich in history and a must-visit for those interested in America’s beginnings. Attractions like Plymouth Rock and the Mayflower II glimpse the Pilgrims’ journey and settlement. Plimoth Patuxet Museums provide a hands-on experience of 17th-century life, showcasing Pilgrim and Native American cultures. The town also features a vibrant waterfront with shops, restaurants, and scenic harbor views. Plymouth combines educational experiences with modern amenities, making it an enjoyable trip for families and history buffs.
Boston Harbor Islands, Massachusetts
Distance: 15 miles to Boston (ferry ride required)
The Boston Harbor Islands offer a peaceful retreat just a short ferry ride from Boston. Popular islands like Spectacle Island and Georges Island feature hiking trails, historic forts, and picnic areas. The islands are also perfect for kayaking and birdwatching. The views of the Boston skyline from the islands provide a stunning backdrop for outdoor adventures. Visiting the Boston Harbor Islands is an easy and unique way to enjoy nature while staying close to urban amenities.
Rockport, Massachusetts
Distance: 50 miles
Rockport is a charming coastal town known for its artistic flair and breathtaking scenery. Bearskin Neck, a narrow peninsula lined with shops and restaurants, is a great place to explore. Halibut Point State Park offers stunning views of the rocky coastline and ocean. Rockport is also home to the iconic Motif No. 1, a historic fishing shack and a popular subject for artists. Its relaxed atmosphere and scenic beauty make it an ideal destination for a quiet weekend escape.
Rockport is a charming coastal town known for its artistic flair and breathtaking scenery. Bearskin Neck, a narrow peninsula lined with shops and restaurants, is a great place to explore. Halibut Point State Park offers stunning views of the rocky coastline and ocean. Rockport is also home to the iconic Motif No. 1, a historic fishing shack and a popular subject for artists. Its relaxed atmosphere and scenic beauty make it an ideal destination for a quiet weekend escape.
Connect with the Westwood Real Estate Expert, Elena Price
When it comes to real estate, you deserve the best, and Elena Price is here to deliver just that. Elena is ranked in the top 1% nationwide and was the #1 Coldwell Banker Realty agent in New England for January and February 2024. Elena’s impressive credentials don't stop there. Elena is also the #4 agent company-wide and the #1 selling broker in Westwood by volume. Recognized by RealTrends as one of "The Thousand" Top 25 U.S. Real Estate Agents in 2023, Elena has over $1 billion in real estate sales.
Contact Elena Price today and experience the exceptional service and results of working with one of the country's most sought-after agents.
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