Ultimate Connecticut Fall Foliage Road Trip Guide Last Updated: September 2023

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Connecticut has some of the most stunning fall colors on the East Coast, making it the perfect place for a fall foliage road trip. In honor of leaf peeping season, we’re sharing our top Western Connecticut fall foliage hikes, viewpoints, bridges, and scenic drives in this ultimate guide to fall foliage in Connecticut. For additional trip planning resources, make sure to check out CTvisit for more information on exploring the beautiful state!

Before getting into the details, when heading to explore Connecticut this fall, please make sure to follow all the Leave No Trace principles to keep Connecticut beautiful! Stick to the trails, take your trash, keep wildlife wild, be fire aware, and share the outdoors respectfully! Especially during peak foliage season, the New England region sees a lot of crowds, so we can all do our part to keep the state as clean and preserved as possible for others to enjoy in the future.

Planning Your Fall Foliage Road Trip

Here are our top tips for planning your own fall foliage road trip around the gorgeous state.

Best Time to Visit Connecticut for Fall Foliage

Historically, the best time to visit Connecticut for leaf peeping is mid-October to early November. Each year, foliage conditions do vary based on weather, drought, and storms, so it’s important to consistently track the foliage before you go. The key to a perfect fall foliage road trip around this area of New England is to be as flexible as possible with your itinerary since peak season can come and go very quickly.

Our biggest tip is to keep an eye on fall foliage trackers as they are updated each week, and to check on Instagram to see live updates from those visiting in the area in terms of color levels.

Leave Room for Leaf Peeping Spontaneity 

Make sure to leave time to explore random scenic byways, public roads, and/or lakes you may stumble upon! We found so many incredible pops of fall foliage color that we didn’t originally have on our itinerary by intentionally getting lost and spontaneously following the colors as we encountered them.

How to Get Around Connecticut

Although there is public transportation available, we’d highly recommend renting a car or Turo for your Connecticut fall foliage road trip. Having a car gives you the flexibility to adjust your plans if the fall colors aren’t optimal in certain areas at particular times.

Wildlife on Connecticut Fall Foliage Hikes

The northwestern side of Connecticut has a ton of wildlife. You will likely be hiking in bear territory during this road trip, so make sure to be bear aware and follow all recommended precautions while out in the forest.

Drone Photography Regulations in Connecticut

As photographers, it’s important to note that Connecticut unfortunately strictly prohibits the operation of drones in all State Parks and State Forests. You may apply for a special use permit; however, don’t plan on using your drone to capture the beautiful foliage in any of these regions. You can use it throughout the state off of those state-owned premises though as long as you have the proper certifications, licenses, and are following local regulations.

Best Ways to See the Fall Foliage in Western Connecticut

Scenic Leaf Peeping Drives in Western Connecticut

Driving through Connecticut’s various state forests is one of the best ways to catch the fall colors in action. Some of the forest roads have the best, most uncrowded, and untouched views of the foliage. Mohawk State Forest and People’s State Forest were two of our favorites for driving around and taking photos of the leaves.

Best Hikes to See Fall Foliage in Connecticut

Something super unique to Connecticut’s fall foliage hikes is how you can find some incredible leaf peeping along hikes to old, abandoned towers & castles! We had never seen anything like this before coming from the West Coast.

Haystack Tower

Enjoy a short scenic walk through the fall colors up to Haystack Mountain Tower. The tower offers 360-degree panoramic views of the whole region from above!

Mount Tom State Park Tower

This was our favorite of the towers that we hiked to in Western Connecticut. The Mount Tom Tower hike takes you up a small incline to overlook a gorgeous lake below. This region had great fall colors for mid-October. Make sure to download the trail data ahead of time as when it is leaf peeping season, the trail can get covered in fallen leaves and is slightly harder to follow. We’d recommend using All Trails or Gaia.

Castle at Talcott Mountain State Park

Talcott Mountain State Park is one of the most popular state parks in Connecticut, and for good reason. Take the Yellow Trail up to Talcott Mountain’s Heublein Tower and you’ll be enveloped in the beautiful foliage for the first half of the hike on the incline. Once you reach the top of the trail, the tree line opens up for some incredible views.

Jessie Gerard Trail

Located in the People’s State Forest, the Jessie Gerard Trail is one of the best hikes in Connecticut for leaf peeping. Rated as moderate with some incline, the views up at Chaugham Lookout are unparalleled, especially if you catch it when the leaves are peaking!

Make sure to start the trail earlier in the morning since there is limited parking available. Also, make sure to wear proper hiking shoes and, if you like, bring hiking poles, since the trail is fairly slippery next to the flowing rivers.

Chauncey Peak Trail

The Chauncey Peak Trail is a 2.2 mile loop that gives you stunning views above the tree line of the reservoir in Meriden. We’d recommend doing the trail counterclockwise to avoid having to go down the steeper rock walls, although this does mean that most of your elevation gain is in the beginning of your hike.

We’d recommend going at sunrise or sunset to capture the leaves here. We went at sunset, and it was perfect for prime golden hour photos of the area.

Other Stops for Your Road Trip Itinerary

Matthies Memorial Park in Beacon Falls

This is one of the most unique places to see fall colors. There’s an abandoned house in the middle of the lake here which makes for incredibly picturesque photos when the surrounding leaves are changing colors.

Hidden Valley Preserve & Thoreau Bridge

The Thoreau Bridge is a beautiful old 134-foot-long suspension bridge in Hidden Valley Preserve. You can add it as a part of your hike to the Memorial Bridge following this trail. The bridge is inscribed with famous quotes from the late author and is a hidden gem among the fall foliage lookouts in Connecticut.

Bulls Covered Bridge

The East Coast is full of various covered bridges throughout the New England region. The Bulls Covered Bridge is right next to the Kent Falls State Park Area that was built back in 1842. It’s one of Connecticut’s few remaining functional covered bridges.

Lovers Leap Bridge

Lovers Leap Bridge is a very photogenic red lenticular truss bridge over the Housatonic River located in Lovers Leap State Park in New Milford, Connecticut.

Finalizing Your Fall Colors Trip to Connecticut

Of course, there are many other beautiful hikes, scenic drives, and bridges in Connecticut to catch the changing leaves. However, if you only have a weekend or a few days, this guide is perfect for a quick road trip to see some of the highlights.

If you have more time to explore western Connecticut, you can add on hikes such as the Sleeping Giant Trail, Bear Mountain, Rattlesnake Cliff, Castle Craig and more hidden gems around the area to extend your leaf peeping adventure.

Overall, you should definitely add a Connecticut Fall Foliage Road Trip to your bucket list. Enjoy getting immersed in the beautiful yellows and reds. For more information on planning your fall colors activities, check out CTvisit for more fall trip planning resources.