Connecticut Fall Foliage Driving Routes: 8 Favorites

There’s nothing quite like fall in Connecticut.

It’s a magical time of year that brings dazzling colors and mesmerizing landscapes to the fore.

Timing a trip to Connecticut to coincide with the tumbling of golden, scarlet, and mocha leaves is always a brilliant idea.

We’re sure you’ve heard all about New England in the fall.

• Instagram posts
• And coffee table books of Connecticut fall foliage

Here’s a guide to our favorite Connecticut fall foliage driving routes.

The best fall foliage driving routes in Connecticut

Connecticut is blessed with some of the finest, most awe-inspiring fall scenery on the planet. A veritable treasure trove of seasonal scenes, this is the place to be if you’re keen to experience this wonderful season in all its glory.

Map design by Stanton House Inn

At Stanton House Inn, we’re ideally placed to enjoy some of the most fabulous fall foliage driving routes in the state.

We urge our guests to get out and about and enjoy the ever-changing palette of colors that comes alive against the backdrop of clear, crisp skies. There are hundreds of routes that afford breathtaking scenic views, but some are extra special.

Here’s a few of our favorite driving routes, starting with road trips on scenic byways that are local to us in Greenwich.

1) Merritt Parkway

Greenwich to Milford, Connecticut

One of the best-loved drives in the state, the Merritt Parkway comes alive in the fall, as the trees change color.

Picture it:

The trees and ground are covered by a patchwork quilt of orange, terracotta, golden, yellow, maroon, and brown.

The route, a limited access parkway, is nestled in the heart of Fairfield County. It runs from the border with New York in Greenwich to Stratford’s Housatonic River. This road is not accessible to trucks and buses, making it a much calmer drive.

And as a designated scenic byway, it’s an idyllic stretch that showcases New England in the fall at its finest. Famed for its natural beauty, brought to life by an abundance of imposing trees, this route is also known for its collection of Art Deco bridges. These unique structures were built during the 1930s and 1940s and they add to the stunning aesthetic of the scenery.

If you’re keen to travel further afield and explore more of the local area and its spectacular fall foliage vistas, there’s more to explore. It is possible to head north from the Merritt Parkway and make for the towns of Danbury and New Milford. As such, you can drive a loop which takes you back south to Fairfield County and the Merritt Parkway.

En route to the Merritt Parkway, there are several places to stop and enjoy the autumnal scenery. An easy stop in is the Greenwich Audubon Center. Further along the route, leaf peeping is a popular activity at the nature centers in New Canaan and Stamford. And of course the Bartlett Arboretum is a highlight for any fall itinerary.

2) Greenwich to Litchfield Hills

• Tiny, charming villages
• Rustic churches
• And rolling hills flanked by trees decorated with sunset-hued leaves

This is a perfect drive to capture photographs and get a sense of why people from every corner of the globe rave about fall in New England.

Starting off in Greenwich, the drive will take you along the coast before heading north on Routes 7 or 8. The jaw-dropping colors are the main draw of this route.

For those keen to combine sightseeing with snapping away and enjoying the views, there are several points of interest to enjoy en route:

• Kent Falls State Park
• Bull’s Bridge
• The West Cornwall covered bridge
• Mohawk State Forest

In fact, more than a few of the best state parks in Connecticut are situated in Litchfield County. And the views are spectacular this time of year.

At the end of the trip, you can always take Route 44 east towards the Connecticut River Valley. Exploring the various attractions, activities, and things to do in Hartford, CT, would be an ideal cap to the trip.

3) Route 136

Westport to Easton, Connecticut

Route 136 is a historic track, which locals call a back road. While this drive may not ease the fastest travel times, it’s a fabulous route to enjoy fall foliage. Covering 20 miles of prime Fairfield County territory, this stretch of tarmac affords incredible views. And once you’re away from the coast, it’s wonderful to be able to experience the isolation and peace of being off the beaten track.

Route 136 ends close to Devil’s Den Preserve, which has the best fall hiking trails for fall foliage views in Connecticut.

4) Route 7

Norwalk to West Cornwall, Connecticut

Route 7 starts in urban Norwalk along the coast before heading inland and uphill.

• New Milford
• Kent
• And even Great Barrington, Massachusetts

5) Connecticut River Valley

Round trip from Middletown, Connecticut

One of the last great places in the world according to National Geographic is of course a major destination for fall foliage season.

An ideal point to begin your exploration is from Middletown, Connecticut. So called for being at the midpoint of the Connecticut River between Old Saybrook and Hartford, Middletown is the first major city on the river. It’s also a college town, hosting Wesleyan University, and a cute downtown.

And the Connecticut River is one of the few in the world without a port at its mouth, so heading south from here will lead to more tranquil environs.

Follow Route 9 south to Route 154. You’ll pass through Haddam along the Connecticut River and reach the ferryboat crossing to East Haddam.

If you’re not feeling a ferry (or when the ferry isn’t running), you can cross the river on Route 82 and pass through downtown East Haddam.

Be sure to visit the eccentric medieval creation of Gillette Castle State Park, one of the most unique attractions in all Connecticut. The commanding view of the river will provide plenty of fall foliage photo opportunities.

• One of the most haunted places in Connecticut
• Or you may have an uneventful hike leading to one of the most beautiful waterfalls in the state

From there, continue south on Route 156 through Lyme. You can make a stop at the Florence Griswold Museum, one of the best museums in CT, before crossing west on I-95.

Head north through the charming Connecticut towns of Essex and Chester before returning back to Middletown, where it all began.

6) Route 169

Lisbon to Woodstock, Connecticut

This route heads straight through the center of what’s called the Quiet Corner of Connecticut.

This 32-mile National Scenic Byway passes nearly 200 historic structures built before 1855. And most importantly, it runs through one of the most untouched natural areas on the East Coast.

The route officially starts to the south in Norwich. That said, skip the city (aside from visiting Yantic Falls) and begin your trip in Lisbon, Connecticut.

The National Scenic Byway doesn’t start until there, anyway.

Take your time driving through the historic and charming towns of:

• Canterbury
• Brooklyn
• Pomfret

Before finishing your drive at Woodstock, just south of Massachusetts. Be sure to visit Roseland Cottage, a Gothic Revival house constructed in 1846 that’s most famous for its unique color.

Westchester County

We’re close to the border with New York. And in this writer’s opinion, it’s well worth crossing the lines to explore scenic drives and leaf peeping hotspots in nearby Westchester County.

Towering trunks line the roads that lead to Kingsland Point Park.

And it’s possible to enjoy panoramic views of Hook Mountain and the Palisades from the Tappan Zee Bridge. The Hudson River walk is also a perfect spot to stretch your legs and get some fresh air after your drive.

A few other options include:

7) Taconic State Parkway

8) Route 9 along the Hudson River

While often busy as it follows the Hudson River, Route 9 winds through the riverside towns of Westchester County.

It passes historic sites like Kykuit and Sunnyside. It also provides a glimpse into beautiful towns like Tarrytown, Sleepy Hollow, Cold Spring, and Beacon. It’s also passes through Hudson Highlands State Park.

At any time you like, you can easily cross one of the bridges across the Hudson River and continue south along the western shore.

This writer highly recommends the Bear Mountain Bridge for its rustic beauty.

9) Route 6, heading east from Peekskill

• Sweeping views of reservoirs
• Quiet small towns
• And fall foliage galore

10) Leaf peeping in the local area near Greenwich, CT

It’s blissful to drive for miles and miles at a languid pace in pursuit of the best fall foliage shots in Connecticut. Yet the Greenwich area is blessed with such spectacular scenery that you don’t have to plan a week-long road trip to enjoy the views. Close to the heart of downtown Greenwich, there’s a host of tracks, routes, and paths you can take on foot or on two or four wheels. For the best hiking to discover the best fall foliage views in Greenwich, we recommend the Mianus River State Park and Babcock Preserve.

Making the most of fall in Connecticut

Fall is the most magical time of year to visit Connecticut, and we’re on hand at Stanton House Inn to ensure guests make the most of the season.

There are always events going on in Greenwich and other local towns.

You can get involved in all sorts of fall activities in Connecticut, everything from:

• apple bobbing
• choosing the best pumpkins at the patch
• fall hiking
• cycling
• taking part in community festivals and gatherings
• corn mazes

And if you’re looking for even more road trip ideas, check-out some of our other guides:

• Wineries on the Connecticut Wine Trail
• Connecticut breweries
• Charming towns throughout the state
• The best CT hiking trails for waterfalls, views, or whatever appeals to you

Regardless, we hope you enjoy wherever the road takes you!

Updated and republish: August 12, 2022