Walker Brook Loop - Brookfield CT Gravel Route
Words and photos by Dave Malwitz
ROUTE HIGHLIGHTS
NAME Walter Brook Loop
START Brookfield Town Center District
DISTANCE 65 miles (105k)
ELEVATION 5,000 ft
SURFACE 40% unpaved gravel and singletrack / 60% paved
RESUPPLY 1 Roxbury Market and Deli (mile 26)
RESUPPLY 2 The Smithy Cafe, New Preston (mile 36, closed Tue/Wed)
BEST SEASON Spring through fall
The metric century is a fantastic distance to get to know a place by bike, and gravel riding is the best way to experience it, especially in Connecticut. If designed correctly, a metric route takes around 5 to 6 hours to complete, giving you plenty of time to see a whole lot. Take it slow and enjoy the farm stands, cafés, markets, barns, rivers, and cool street names as you pass through.
Growing up in Brookfield, Connecticut, we used to camp by the river, mountain bike through the woods, and bushwhack up hills. I always loved exploring, but the gravel bike opens up entirely new possibilities. With that in mind, I set out to build a 100K route starting from Brookfield’s Town Center District. It crosses both sides of the Housatonic River and strings together some of the best gravel across three neighboring counties in a single ride: Fairfield, New Haven, and Litchfield.
This Connecticut gravel route is 65 miles with 5,000 feet of climbing, and nearly 40 percent unpaved. I rode it just after a heavy rain, and the roads drained well with no water crossings to worry about. It's best experienced from spring through fall. and keep an eye out for wildlife; someone even stopped to warn me of a bear they saw nearby. These photos were taken when I rode the route in early August, 2026.
Finding Waldo
The route starts from the Brookfield Town Center, where there is plenty of parking near the Four Corners area. Heading south, the first gravel starts at mile 6 with Tamarack and Sanford Roads, just before the Glen Road Silver Bridge over the Housatonic. Two miles up the road and you’ll pass Mitchell Farm, a 9th and 10th generation family farm that operates during all four seasons.
Take the road climb up and you’ll find George C. Waldo State Park in Southbury, you’re first optional detour. Waldo is 150 acres on the banks of Lake Lillinonah, with a stretch of singletrack that's a blast to ride on a gravel bike. It includes a few log rolls and rock sections that you may need to walk, but a fun challenge. Skip it if you'd rather not dismount.
Peachy Keen
From the park, the route turns north toward Roxbury on some classic New England gravel: Peach Orchard Road, Flag Swamp Road, Rocky Mountain Road. Mile 26 brings the Roxbury Market and Deli, first resupply of the day that you won’t want to miss. I grabbed homemade chocolate chip cookies and topped off my water.
North of Roxbury is the heart of the route: seven miles of gravel starting along the Shepaug River on Judds Bridge Road, across Judds Bridge, then onto Walker Brook Road. Quiet, scenic, right along the water most of the way.
New Preston Pie
Walker Brook carries you into New Preston, where the Smithy Cafe at 9 Main comes at mile 36. This small town gathering spot is our second resupply, and worth the stop for the berry pie and coffee alone. Closed Tuesdays and Wednesdays, plan around it. From there, swing by Lake Waramaug State Park, a popular local spot for swimming, camping, and paddling.
River Rush
From the lake the route turns west, back through New Milford with a few more gravel stretches and the last real climbing of the day. In Gaylordsville, head south and pick up River Road along the Housatonic, fast and fun gravel down into downtown New Milford.
Go fast and stay to the right along Grove Street with its small shoulder. Drivers generally give plenty of room as it’s well traveled by cyclists. From there it's back to Brookfield, where the Town Center District has plenty of food and drink to close out the day.
Hope you get a chance to experience some of these great Connecticut roads while tasting some local flavors, meeting a few people, and enjoying views that make this one of my favorite gravel routes on the East Coast.
We tested the Sweet Protection Falconer 2Vi Mips, Smith Trace Mips, and POC Amidal across style, fit, features, colors, and weight, and found the POC Amidal to be the strongest all-around gravel helmet in the $250-300 range.