Great, Rustic and Colorful Tours for the Peak Season in Connecticut

This and all of the state tour pages will be updated periodically throughout the fall. As the other seasons arrive, tours for them will be added as well, so it's important to check back here often. New tours will be added to the top of the page, so you won't have to scroll. We suggest that you bookmark this page so you can find it quickly and easily.

Tour One
Ridgefield, to Kent and Litchfield

One of the finest places to drive and take in a countryside that’s still agrarian in nature is to start in Ridgefield, Connecticut, home to many old and beautiful houses and a hearty collection of trees with gorgeous leaves, to Kent, which has its share of historic houses and the Kent boarding school, and then to Litchfield, where the commons is so typically New England it could be a truly representative diorama in a New England museum in the decades to come.

Litchfield is the site of the first law school in the country, a school some of our founding fathers attended the town's history is and jealously preserved. Modern amenities are accessible but not gaudily obvious. Most of the restaurants offer some wonderful fare and if you'd like to spend the night here, there re some beautiful B&Bs, inns and hotels.

The tour takes you through some really beautiful, hilly countryside that provides a breath-taking New England fall foliage spectacle year in and year out. Horse farms abound, and while it’s great in the fall, it’s not the best place to be during mud season in the spring.

The roads in the area give rustic its definition, and the sprawling, hilly countryside offers a tremendous amount to take in, so be sure to have your camera at the ready. For tips on taking photographs of New England fall foliage, visit our Gallery Page.

This will be a two-leg tour, from Ridgefield, in northern Fairfield County, to New Milford and then winding up in Litchfield, in Litchfield County, a town very rich in history and grandeur. You can take the same route back to Ridgefield, or drive around either the Litchfield or Kent areas.

We start by going north on Route 35 (Main Street) for about 3 miles, then taking a LEFT onto Route 7.

This remarkable road has been a contentious stretch of asphalt for some time in Connecticut—more than 40 years' worth. Super 7, which was to go at least to the border of Massachusetts when the grand plan was set before the town and state governments back in the '60s, was built as far as Norwalk. But, after numerous court cases and other battles, it remains a 2- and sometimes 4-lane highway well short of a finished Super 7. If you stay on it, however, it will take you all the way up through Vermont to Canada.

Stay on Route 7 until Exit 20. Turn RIGHT at Federal Road (which is also Routes. 202 and 7) and continue to follow it for about 7 miles until you see Bridge Street.

Turn RIGHT toward Bridge, go a short distance, and then turn LEFT at Main Street. You will be in New Milford. It’s about a 30-minute drive, barring any construction or other problems, and it’s a nice place to stop for lunch.

Leg Two
From New Milford to Kent, drive southeast on Main Street and then RIGHT at Bridge Street for a short distance and then turn RIGHT onto Route 7 (also called Kent Road). Stay on this for about 14 miles until you get to Kent, then turn RIGHT on Green Ward Way, and then soon after that onto Kent Green Blvd.

Leg Three
From Kent to Litchfield, from South Main Street, turn LEFT onto Route 341. You'll go through East Kent, Warren and Woodville. A little past Woodville, Near Mt. Tom State Park, Route 341 becomes Route 202, which curves sharply LEFT and north. Stay on Route 202, which becomes Bentam Road. At the intersection with South Lake Street on your LEFT, it becomes West Street and takes you RIGHT into Litchfield.

The total time for all three legs is about 1:30. There are a number of great restaurants at which you can eat lunch or dinner depending on when you arrive, and if you'd like to stay in the Litchfield area for the night to do some local exploring, there are some nice accommodations.

Tour Two
Waterbury to Black Rock State Park to Southbury and Return to Waterbury

Obviously, this takes you through the central part of the state and lets you see some more hills as you get to Southbury. Past falls there have been really beautiful, with lots of yellow leaves. Black Rock State Park has some wonderful views itself. You'll find it to be a pleasant fall oasis amongst some of Connecticut's mid-state cities, such as Waterbury.

Leg One
From Waterbury, take Route 8 north to Exit 38 at Reynolds Bridge. Take a LEFT at the exit ramp bottom onto Route 6 heading south. Stay on Route 6 until you see the sign for Black Rock State Park. This is a really wonderful place to take in the scenery and you’ll want to take a lot of pictures here, especially during the peak season.

Leg Two
When you leave the park, take a LEFT to get back on Route 6 South to Route 8, the same way you came. Take Route 8 down to Route 84 and get on Route 84 heading west Get off Exit 15 (Main Street North) to Southbury. Here the hills are higher and you’ll be able to get some spectacular views as you drive through the town. When you’re ready to return to Waterbury, drive south on Main Street North, go under Route 84, then take a LEFT to get back on Route 84 headed east Get off Route 84 at Exit 22. At the bottom of the ramp take a RIGHT onto Meadow Street and take that to Waterbury. Total drive time is about two hours.

Tour Three
Old Lyme to Hadlyme

Old Lyme is one of the most historic towns in Connecticut, with a Main Street that takes one back as if through a time machine to the 1700s,. The street is straddled by magnificent Federal houses and great old Colonials, some dating back to the 1700s. At one end is an historic church and along the street, small shops that blend in with the antique architecture of the village.

And yet just off Main Street, Old Lyme has two attractive strip malls for a bank, large, upscale A&P, a large pharmacy, real estate and other offices and restaurants. It’s as if it’s a town, like so many in New England, that can allow the past to coexist peacefully with the present. That's because the town is run by people who are adamant about protecting the past.

The drive to Hadlyme is easy and very scenic. In fact, this is one of our all-time favorite tours during autumn, despite the utter magnificence of Vermont’s mountains.

Start on Route 156 north for about 4 miles, then take a slight LEFT onto Mt. Archer Road (Route 86) off of 156. When you reach Hadlyme, it’s every bit as quaint as Old Lyme, except considerably smaller. The houses are beautiful and date back centuries. But the leaf colors along this route are simply amazing. When you reach Hadlyme, we recommend that you take a LEFT on Ferry Road until its end at the Connecticut River. You’ll travel along a road with spectacular trees on your RIGHT and marshland full of cattails on your LEFT. At sunset or sunrise, this is one really gorgeous place to be.