Brookfield, Conn., is in a prime location for short getaways. Access to scenic coastlines, bustling cities, and quiet rural towns gives you many options for an easy weekend adventure. These destinations are all within a reasonable driving distance and offer different activities, food scenes, and places to explore. If you're looking for a change of pace, these spots can help you recharge without requiring too much planning.
Each location listed here offers a unique experience, from beach walks to mountain hikes to exploring local culture. Here are nine excellent ideas for weekend trips from Brookfield.
New Haven, CT (32 miles)
New Haven is known for Yale University, but it also has a growing food scene and several museums. The Yale University Art Gallery and the Peabody Museum are open to the public. The city’s compact downtown includes pizza spots, cafes, and independent movie theaters. You can also walk through the campus grounds, explore nearby parks, or try local breweries. Be sure to visit Lighthouse Point Park, an 82-acre waterfront park offering stunning views, a beach, scenic hiking trails, and a historic carousel. New Haven is 60 minutes away, making it one of the most convenient options for weekend trips from Brookfield.
Cold Spring, NY (47 miles)
Cold Spring is a small village along the Hudson River with scenic views and easy hiking access. Breakneck Ridge and Hudson Highlands State Park draw outdoor enthusiasts. The village center includes restaurants, antique shops, and small art studios. Visitors often walk along the river, browse local shops, and enjoy the surrounding nature. The town is less than an hour away and offers a simple but satisfying weekend option.
The Berkshires, MA (78 miles)
The Berkshires offer rolling hills, art museums, and hiking trails. This region of western Massachusetts draws visitors year-round. In warmer months, trails at Monument Mountain or Mount Greylock offer rewarding views. During the fall, the landscape becomes a colorful display of changing leaves. Cultural spots like the Norman Rockwell Museum, MASS MoCA, and Tanglewood appeal to art and music fans. Local towns such as Lenox and Great Barrington feature independent shops and relaxed cafes. The Berkshires are about a two-hour drive, making them one of the most accessible weekend trips from Brookfield.
Hudson, NY (86 miles)
Hudson has developed into a destination for antique shopping, modern dining, and art galleries. The town’s Warren Street is lined with design studios, wine shops, and cafes. Hudson’s train station also makes it easy to access the city from other parts of New York State. Many visitors choose to stay in boutique hotels or historic inns. There are also trails and riverfront views that add to the experience. The drive from Brookfield takes around two hours, offering a smooth ride into the Hudson Valley without going far.
Mystic, CT (95 miles)
Mystic is a small coastal town that offers both history and waterfront activities. The Mystic Seaport Museum and the Mystic Aquarium are popular stops. Walking through the historic downtown gives you access to restaurants, bookshops, and stores focusing on locally made goods. Boat rides, seafood dining, and boardwalk strolls are common ways to enjoy the area. Mystic’s compact layout makes it easy to explore on foot.
Northampton, MA (99 miles)
Northampton is a small college town with lovely bookshops, coffee houses, and record stores. Smith College gives the town an academic feel, and the Smith College Museum of Art is open to the public. Live music venues and casual restaurants are also part of what makes Northampton interesting. The town supports local businesses and has a walkable layout encouraging relaxed exploration. It's about a two-hour drive from Brookfield, offering something new without much effort.
The Catskills, NY (117 miles)
The Catskills are known for their natural scenery and outdoor activities. Travelers can hike trails in places like Kaaterskill Falls or explore North-South Lake. In recent years, towns in the area have gained attention for new restaurants, cafes, and small music venues. You can also check out local breweries, farmers markets, and lakeside cabins. The Catskills are close enough to work as a weekend destination but still feel like a complete escape.
Newport, RI (139 miles)
Newport is a coastal city known for its historic mansions and walkable waterfront. Visitors enjoy touring the famous Cliff Walk, a paved path that runs alongside the ocean and behind several old estates. The city’s small harbor is lined with restaurants and boutiques that stay busy throughout the year. You can visit the Newport Mansions, including The Breakers and Marble House, which provide a look into the city’s Gilded Age past. The area also hosts art galleries and events focusing on music, sailing, and local food.
Montauk & Sag Harbor, NY (171 miles)
Montauk sits at the eastern end of Long Island and offers wide beaches, seafood restaurants, and quiet roads. It’s more relaxed than nearby Hamptons towns, making it appealing for visitors who want to avoid heavy crowds. Activities like hiking in Montauk Point State Park or visiting the lighthouse are good ways to fill the weekend. The town also has casual hotels and cozy inns near the water. Reaching Montauk takes a little more time, about three hours, but the coastal setting makes the trip worthwhile.
Just 35 minutes from Montauk is Sag Harbor, NY. Sag Harbor is a charming town known for its beautiful beaches, excellent restaurants, and unique shops. Enjoy a leisurely stroll past the iconic Windmill or explore over 100 historical homes in the village. Don’t miss the opportunity to visit the Sag Harbor Whaling and Historical Museum, which offers a fascinating glimpse into the area's maritime history. Combining Sag Harbor with Montauk makes for an ideal weekend getaway full of scenic beauty and cultural richness.
Just 35 minutes from Montauk is Sag Harbor, NY. Sag Harbor is a charming town known for its beautiful beaches, excellent restaurants, and unique shops. Enjoy a leisurely stroll past the iconic Windmill or explore over 100 historical homes in the village. Don’t miss the opportunity to visit the Sag Harbor Whaling and Historical Museum, which offers a fascinating glimpse into the area's maritime history. Combining Sag Harbor with Montauk makes for an ideal weekend getaway full of scenic beauty and cultural richness.
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