Motorcycle Rides in the Northwest Hills of Connecticut

Cruising the Northwest Hills

Motorcycle Ride and Tour of the Northwest Hills of Connecticut

What better way is there to spend a Sunday morning than to go for a motorcycle ride and tour through the Connecticut Northwest Hills?  I find myself drawn there often. The rolling hills and twisty roads with great scenery are a great way to relax and unwind before heading back to work on Monday. The varied choices for wonderful and eclectic eateries provide options to stop and relax while grabbing a coffee or bite to eat. There are many back roads throughout NWCT to choose from, but here is a fairly simple to follow route that will take you across some of my favorite state roads.

Get out early and plan your own ride to Falls Village. Stop in and visit with Greg & Annie at Toymakers Café. This has become quite the place to be for riders on a Sunday morning. Enjoy breakfast and coffee while walking around the parking lot checking out the other motorcycles. Sometimes some rare and unique rides come in. Get there before the large groups roll in and make the kitchen very busy.

Leaving Toymakers, head west on Main St. turn right onto Railroad St and left on Water St. under the tracks and over the bridge crossing the Housatonic River. Make an immediate left onto Dugway Rd. At the end you will be across the street from Lime Rock Park, and will head east on Route 112. At Route 7 head south and in Cornwall Bridge make a left turn onto Route 45 heading south toward Warren.

Turn right onto Route 341 and head west for approximately 3 miles and turn left onto Kent Hollow Rd. In a couple of miles turn right onto Lake Waramaug Rd. (Route 478) and follow to the end. Turn left onto Route 202 for around 6 miles and turn left onto Maple St, which continues as Milton Rd, and ends at Route 4 in Goshen. Turn right onto Route 4 and continue until Route 272, and turn left heading north, continuing to US 44 in Norfolk.

Head west on US 44 to Lakeville, and turn left onto Route 41 heading toward Sharon. By now, it’s been a few hours of riding and you might be getting hungry. If so, make a right onto Route 361 and When Pigs Fly BBQ is right there. Eat or not, the ride continues and will end with a coffee stop in Kent. Take RT 361 back to Route 41 and continue south again. RT 41 crosses into New York State at the stop sign, and turn left onto Amenia Union Rd (Rt 2). Turn left onto Kent Rd (Rt 3) and follow onto Bog Hollow Rd (Rt 3) and back into Connecticut where the road becomes Macedonia Rd / Rt 341. Continue to Route 7 in Kent where the monument is and turn left to find the Kent Coffee & Chocolate Company, or a plethora of other eateries to choose from. Park your steed and hang out – This is where the ride ends… for now.


Map Route


This article has been contributed by Steve Smith with New York native and Waterbury-area resident Steve Smith is a nationally-certified Motorcycle Safety Foundation rider coach and an instructor with the Connecticut Rider Education Program. He has nearly two decades of motorcycle safety experience and during that time has provided training to thousands of beginner and experienced riders. Email him at

No Comments

Post a Comment