Fall in New England means pumpkins and apples, crisp mornings thawing into balmy afternoons, leaves changing color everywhere you look, and – best of all – scenic drives. In recent years, I’ve been testing out the fall foliage driving routes suggested by the Connecticut Department of Energy and Environmental Protection (DEEP.) After trying three Northern Connecticut fall foliage drives and two Southeastern Connecticut fall foliage drives, I’m tackling the loop that comes closest to the part of Connecticut where I first experienced the beauty of fall, happily stomping over crunchy leaves and “helping” to clean them up with a child-sized rake. At the time, I took New England’s autumnal splendor for granted, but now, like everyone else, I seek out ways to celebrate this most fleeting of seasons. This driving route is as good as any to soak up all that spectacular color before it’s gone.
As with the previous routes I’ve tested, parts of this one completely flummoxed me when I first set out with DEEP’s directions. So in this post, as in the previous posts linked above, I’m providing my own directions which are, I hope, much easier to follow. (To use DEEP’s original directions, click here.)
Western Towns Loop
DEEP calls this loop “Scenic Fairfield,” and on the map, it looks fairly straightforward. Covering approximately 115 miles, it begins in New Canaan and travels up through western Fairfield County, across the southern tip of Litchfield County, then back around. But once you exit the Merritt Parkway and start driving north, it dawns on you that this one is going to take a while. Along the way, picturesque town centers and expansive lakes tempt you to linger. Numerous state parks and local nature trails beckon. You realize, as you drive, that this route cuts through some of Connecticut’s most bustling towns as well as some of its calmest farmland, and there are so many opportunities to stop and explore that it’s actually slightly overwhelming. (In a few spots there can be a lot of traffic, too, so keep that in mind when planning!) But if you leave enough time – anywhere from half a day to a long weekend, depending on how much you want to squeeze into the trip – you’ll be rewarded with a diversity of landscapes and abundant foliage. From busy New Milford and Newtown to quiet Sherman; from the well-traveled commercial routes of Danbury and Woodbury to the forgotten-feeling back roads of Roxbury, this drive is a good choice for anyone wanting to experience the variety of southwestern Connecticut. Because it passes straight through so many town centers, it’s also easy to incorporate shopping (from high end boutiques to antique shops to farm stands) and dining into your trip. And because this part of the state tends to reach its full fall color later in the season than the rest of the region, you can catch the foliage changing here long after most of New England has passed its peak.
From the Merritt Parkway (Route 15) southbound, take Exit 38. Turn left onto Route 123 North towards New Canaan. Turn right on Route 106 North, then left onto Route 7 North in Wilton and continue through Ridgefield into Danbury. Take I84 East/Route 7 North to Exit 5. Continue on Downs Street. Turn left on Main Street/Route 39, then turn right onto Golden Hill Road. Turn left onto Route 37 North towards New Fairfield. Turn right onto Route 39 North. In the center of Sherman, turn right onto Route 37, then follow it until you reach Route 7. Turn right on Route 7 South, then turn left onto Route 202/Bridge Street to cross the river into downtown New Milford. Turn right onto Route 67 East to Roxbury. (From here, you can take a right onto Route 133 to take a short detour into the center of Bridgewater.) From Route 67, stay to the left to continue on Route 317 South. In Woodbury, turn right onto Route 6 West, and follow it to I84. Take I84 West to Exit 10 to get back on Route 6 West. Turn left onto Route 25 South in Newtown. Turn right on Route 302 West. In Bethel, turn left on Route 58 South. Turn right onto Route 136 South in Easton, and follow it to get back on the Merritt in Westport.