By Bowman Properties
Some of the best scenery in western Connecticut sits within a short drive of downtown New Milford, CT. Whether you have an afternoon or a full day, the scenic drives near New Milford, CT, take you past the Housatonic River, covered bridges, waterfalls, and the rolling hills of the Litchfield countryside. We have driven these roads in every season, and we want to share the routes we send visitors and neighbors on again and again. Here are our favorites, along with the stops that make each one worth the trip.
Key Takeaways
- Route 7 north follows the Housatonic River past Kent Falls and historic covered bridges.
- The Litchfield Hills loop runs southeast on Route 67 through Bridgewater and Roxbury, then north toward Washington and Lake Waramaug.
- Lovers Leap State Park offers a scenic drive and a photogenic bridge minutes from downtown.
- Early to mid October is the top window for fall color in the Litchfield Hills.
Along the Housatonic River on Route 7
Route 7 north out of New Milford is one of the most rewarding scenic drives near New Milford, CT. The road hugs the Housatonic River as it climbs toward Kent, with water on one side and wooded hills on the other. It is an easy route to follow and hard to beat for classic New England views.
Kent sits about 20 minutes north and rewards the drive with Kent Falls State Park, home to the tallest waterfall in the state. The stretch between New Milford and Cornwall also passes two of Connecticut's beloved covered bridges. If you have more time, keep going past Cornwall toward Sharon, where the valley opens into some of the quietest countryside in the region.
What to See Along the Housatonic
- Kent Falls State Park, with a short walk up alongside a series of cascades
- Bulls Bridge in Kent, one of the few covered bridges you can still drive through
- The West Cornwall Covered Bridge, a red landmark spanning the Housatonic
- River overlooks and pull-offs that are ideal for photos in autumn
The Litchfield Hills Loop on Route 67
For a longer outing, Route 67 heads southeast from New Milford into the heart of the Litchfield Hills. The road rolls through Bridgewater and Roxbury, where one stretch is a designated state scenic road, passing farms, stone walls, and quiet town greens along the way. Many people call this the postcard version of Connecticut, and we agree. Give yourself a few hours, since a wider loop through the hill towns can run close to 100 miles once you factor in stops.
At Roxbury, you can turn north on Route 199 toward Washington, then continue to New Preston and Lake Waramaug, one of the largest natural lakes in the state. The area around the lake is a favorite stop for a slow drive and a long look at the water.
Stops Worth Making on the Loop
- The Roxbury and Bridgewater town greens, small and full of character
- Washington Depot, a walkable village with shops and cafes
- Lake Waramaug, with a shoreline road that circles the water
- Hopkins Vineyard in Warren, overlooking the lake from a working farm
Short Scenic Drives Close to Downtown
Not every scenic drive near New Milford, CT, needs a full day. Some of the best views are only minutes from the town green, a long, historic common that anchors downtown and makes a fine place to start or end a drive.
Lovers Leap State Park sits just south of downtown and makes a quick, memorable trip. The park is known for its red iron bridge over the Housatonic River, a favorite spot for photos any time of year.
Quick Drives to Enjoy Close to Home
- The New Milford town green and its historic surrounding streets
- Lovers Leap State Park and its lenticular truss bridge
- Route 202 toward Litchfield for open, rolling views
- Back roads toward Bridgewater for a short country loop
Timing Your Drive Through the Seasons
The scenery here changes with the calendar, and each season gives you a different reason to drive. Fall is the headliner, and the Litchfield Hills tend to turn color a little earlier than the rest of the state.
Spring and summer bring green hills and full farm stands, while winter turns the same roads quiet and open. We suggest planning your route around the light, since late afternoon is often the best time for photos.
When to Take These Scenic Drives
- Early to mid October for peak fall foliage in the Litchfield Hills
- Late spring for blossoms, waterfalls, and green river valleys
- Summer weekends for farm stands and lakeside stops
- Clear winter days for open views without the leaves
FAQs
When is the best time to take a scenic drive near New Milford, CT?
Early to mid October is the top window, since the Litchfield Hills usually reach peak color before southern Connecticut. That said, the Housatonic River routes are worth driving in any season.
Which scenic drive near New Milford is best for a first visit?
We usually point first-timers to Route 7 north along the Housatonic toward Kent. It is simple to follow, and it packs a waterfall, covered bridges, and river views into one easy trip.
Can these drives help me get to know the local real estate market?
Yes. Driving these routes is one of the best ways to see the different pockets of our area, from riverside New Milford to the hill towns beyond. We are always glad to talk through what living in each one is really like.
Contact Bowman Properties Today
The roads around New Milford, CT, are a great way to fall for this part of Connecticut, and we love helping people find a home to match the view. When you are ready to trade the driver's seat for a front porch, we know exactly where to look.
If you have questions about New Milford or the surrounding hill towns, reach out to us, Bowman Properties. We would be glad to help you find your place in the Greater Danbury area.
