By Bowman Properties
One of the best things about living in New Milford, CT, is how easy it is to escape for a quick weekend adventure. We love calling this town home because it offers peaceful small-town living while sitting within a short drive of some of the most beautiful destinations in New England. From quiet countryside inns to lively coastal towns, there’s always somewhere new to explore. Let’s take a closer look at the best weekend trips that make living in New Milford so rewarding.
Key Takeaways
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New Milford’s central location connects residents to top regional getaways.
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Litchfield Hills, western Massachusetts, and Connecticut’s shoreline are all within easy reach.
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Scenic drives, vineyards, and hiking destinations create year-round options.
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Living in New Milford means enjoying both home comfort and nearby adventure.
A Perfect Launch Point for Easy Escapes
New Milford’s location along Route 7 and near I-84 gives residents exceptional access to a range of weekend destinations. In under two hours, you can be hiking, shopping, or dining in a completely new setting—without ever needing to book a flight.
Why New Milford Makes Weekend Travel Simple
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Central Location: Quick highway access makes short trips stress-free.
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Variety of Options: Lakes, mountains, and coastal towns are all within reach.
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Four-Season Appeal: From summer lake outings to winter getaways, every season works.
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Comfort at Home: Returning to New Milford after a weekend trip always feels like coming home.
This convenience is one of the reasons buyers love the town—it delivers both serenity and connection.
Litchfield Hills: Classic Connecticut Charm
Just 30–40 minutes from downtown New Milford, the Litchfield Hills area offers an easy retreat filled with rolling landscapes, boutique inns, and great food. It’s the kind of place where a short drive feels like stepping into another world.
Favorite Spots to Visit
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Topsmead State Forest (Litchfield): Ideal for a peaceful walk or picnic.
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Litchfield Village Green: Shop small boutiques and admire historic architecture.
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Arethusa Farm Dairy (Bantam): A must-stop for fresh ice cream and cheeses.
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Winvian Farm (Morris): Enjoy fine dining or a spa day in an elegant countryside setting.
The Litchfield Hills give New Milford residents an effortless option for weekend relaxation without long travel times.
The Berkshires: Culture and Outdoor Adventure
A little over two hours north, the Berkshires in western Massachusetts combine arts, dining, and outdoor recreation in one destination. It’s close enough for a weekend, yet far enough to feel like a real getaway.
What Makes the Berkshires Worth the Drive
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Tanglewood (Lenox): Experience world-class outdoor concerts each summer.
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Norman Rockwell Museum (Stockbridge): Explore iconic American art.
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Mount Greylock: Hike or drive to Massachusetts’ highest peak for breathtaking views.
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Great Barrington: Discover galleries, local breweries, and farm-to-table restaurants.
For those who enjoy mixing cultural experiences with scenic landscapes, the Berkshires are the perfect weekend retreat from New Milford.
Connecticut Wine Country: Relaxed and Scenic
Many residents are surprised to learn that several of Connecticut’s best wineries are less than an hour from New Milford. These countryside vineyards offer local wine, stunning views, and relaxed atmospheres ideal for a Saturday afternoon.
Wineries Worth Exploring
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Hopkins Vineyard (Warren): Overlooks Lake Waramaug with award-winning wines.
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Sunset Meadow Vineyards (Goshen): Known for its bold reds and weekend events.
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White Silo Farm & Winery (Sherman): Features fruit wines and local art exhibits.
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Haight-Brown Vineyard (Litchfield): One of Connecticut’s oldest, offering tastings and tours.
Each location provides an easy, scenic drive from New Milford—perfect for a relaxed day trip or a romantic weekend away.
The Connecticut Coast: A Change of Scenery
When the ocean calls, the Long Island Sound shoreline is about a two-hour drive south, depending on your destination. It’s a straightforward trip that rewards you with beaches, coastal dining, and charming seaside towns.
Top Coastal Stops for a Weekend Away
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Madison: Visit Hammonasset Beach State Park for a classic beach day.
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Westport: Blend beach time with dining and boutique shopping.
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Mystic: Explore the historic seaport and aquarium for a fun family trip.
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Old Saybrook: Enjoy marina views and relaxed waterfront restaurants.
Each of these spots offers a quick, satisfying escape that pairs perfectly with New Milford’s slower-paced lifestyle.
Close-to-Home Escapes in New Milford
Of course, you don’t always need to leave town to feel like you’ve taken a break. New Milford itself is filled with local gems that make weekends special without any travel at all.
Local Favorites Right at Home
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Candlewood Lake: Boating, kayaking, or simply relaxing by the water.
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Lover’s Leap State Park: Scenic overlooks and easy hiking trails.
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Downtown Green: Dine outdoors or enjoy coffee at one of the local cafés.
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Elephant’s Trunk Flea Market: A Sunday tradition for antiques and local finds.
These local attractions make it easy to spend a weekend recharging right here in town.
FAQs
How Far Are Most Weekend Destinations from New Milford?
Most of the top spots—like Litchfield Hills, nearby vineyards, or the Connecticut coast—can be reached in about one to two hours, depending on traffic and destination.
Are There Family-Friendly Weekend Trips Near New Milford?
Absolutely. Try Kent Falls State Park, Lake Waramaug, or Mystic Seaport for activities the whole family can enjoy.
What’s the Best Time of Year for Weekend Trips from New Milford?
Spring and fall are ideal for scenic drives and outdoor festivals, while summer brings lake days and beach trips. Winter weekends are great for cozy inns and nearby skiing.
Contact Bowman Properties Today
At Bowman Properties, we know that life in New Milford isn’t just about the homes—it’s about the lifestyle that comes with them. Living here gives you the freedom to explore all of New England without losing that sense of peace when you return.
If you’re ready to find a home that makes every weekend an opportunity for adventure, reach out to Bowman Properties today. We’ll help you discover the right property in New Milford so you can enjoy the best of both worlds—tranquil living at home and endless destinations just down the road.
If you’re ready to find a home that makes every weekend an opportunity for adventure, reach out to Bowman Properties today. We’ll help you discover the right property in New Milford so you can enjoy the best of both worlds—tranquil living at home and endless destinations just down the road.
