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Connecticut

The Perfect Connecticut Day Trip Itinerary for Fall

June 2, 2023

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If you’re looking to take a day trip to Connecticut during a New England fall road trip or as a day trip from Boston, I’ve got you covered!

Connecticut is a beautiful New England state known for beautiful fall foliage and as the home of Yale. It was one of the original 13 colonies and is the 3rd smallest US state by land area.

Despite its small size, Connecticut is a great state for outdoor recreation! The state boasts 110 state parks (that’s more than Texas, which is MUCH larger) and 32 state forests. Connecticut ranks number 10 in the nation for the most state parks, which is quite impressive given its size! All this to say that you should be sure to spend some hiking and visiting state parks during your trip to Connecticut, and this itinerary has you covered.

This one day Connecticut itinerary is based on my visit to the area in late fall/early winter 2022. It covers central Connecticut and involves taking a road trip from South to North. The fall foliage was gone, but it was still a beautiful day full of adventure!



Connecticut One Day Itinerary

This itinerary is a mix of hiking with some great spots for food and drink along the way. Check out my beginner hiking tips blog if you’re new to hiking!


Sleeping Giant State Park

Start your day with a popular state park known for rocky trails and sweeping views of the area from the Sleeping Giant Observation Tower.

Lydia scrambling up the blue trail in Sleeping Giant State Park. There is a view of a valley down below in the background.Lydia standing out on a large rock formation with a steep cliff on one side in Sleeping Giant State Park.
The Blue Trail at Sleeping Giant

There are several hikes to choose from based on your abilities. The easiest way to hike up to the tower is on a road. This trail is about 3 miles and uphill, but the path is wide and smooth.

I opted for a more challenging route and took the Blue Trail up to the tower. The Blue Trail includes a lot of scrambling, including a section towards the beginning where you’ll need to climb down a steep area (about 15 feet) with rocks and roots and large steps.

From there, there is a bit more scrambling to reach the top. The high point of the trail has fantastic views and some neat rock formations protruding from the cliff. You’ll be able to look down steep cliff walls and see hikers on the tower road down below.

From here, you can climb down just a bit to connect over to the Tower Trail.

Inside the top of the tower at Sleeping Giant State Park. The building is made of stone and there are 3 windows that show a view of the area.
The tower at Sleeping Giant State Park

The Sleeping Giant Observation Tower was built in the 1930’s and is made up of 3 levels. Instead of steps, ramps will lead you to the top. There are some animal carvings on the outside of the tower and wonderful views from the top.

Note that this area can be particularly crowded, so go early to avoid throngs of people.


Chauncey Peak

If you’re up for another trail, head about 20 minutes up the road from Sleeping Giant and visit Chauncey Peak. Here you can hike around the Bradley Hubbard Reservoir and take in a fantastic view from the top of Chauncey Peak.

Taken from the top of Chauncey Peak, a rocky cliff stands tall above a lake.Taken from the top of Chauncey Peak, Lydia sits on a rocky area with views of the lake and the surrounding valley behind her.
Chauncey Peak

The trail is about 2.2 miles with 350 feet of elevation gain. I went counterclockwise in order to go up the steepest portion. At the top, you’ll hike along the ridge for a bit and get to enjoy continuous views.

There is also an active quarry right next to the peak that you’ll be hiking alongside. It was a bit strange to be so close to mining activity while in a park.

The second half of the loop is an easy walk right along the water. While the quarry takes away from the magic, the views at the top looking down at the reservoir are beautiful and this quick hike is worth the effort!


Kinsmen Brewing

After working up an appetite from hiking, head to Kinsmen Brewing for pizza and beer.

The interior of Kinsmen Brewing. There is a table made from a barrel, round light fixtures and a lot of wood in the details.A pizza topped with veggies and a beer in a wine glass next to it on a table.
Kinsmen Brewing

The Kinsmen Taproom was formerly a bolt factory and has been beautifully renovated and restored using reclaimed materials from the original factory.

Kinsmen serves a variety of beers, mainly being stouts, ales and IPAs. There were a couple sour beers on tap that I enjoyed as well.

They also serve pizza. I enjoyed The Farmer pizza, which was packed with veggies and had great flavor. There is also a small selection of other food items, such as a giant soft pretzel.

The spacious Kinsmen Brewing offers the perfect atmosphere to kick back and relax after a morning of adventure.


Hogan’s Cider Mill

Hogan’s Cider Mill is a must-stop for a bit of shopping, a delicious cider drink, mini golf and more. Their offerings vary based on time of year. In the fall, one of their specials was a spiked hot apple cider with an apple cider donut. In the summer, they offer patriotic special drinks such as the Stars & Stripes Sangria Slushie and a ‘Merica shot.

The exterior of Hogan's Cider Mill. There is a vintage red truck adorned with garland and a red bow. The general store in the background is white.A cup of hot cider topped with an apple cider donut and whipped cream. The cider is in a green, paper cup with artwork depicting Hogan's Cider Mill.
Hogan’s Cider Mill

In addition to a drink at the bar, you can shop in their farm store. It feels like a general store and items include candles, gifts, home decor and local food items.

The golf course next door has the same owners, so you can bring your drinks from the taproom over to the course and play either mini golf or the 18 hole course.

Hogan’s also has a large space for outdoor seating. Whether you enjoy a flight of cider, play a round of mini golf or just take a look around the shop, it’s worth a stop to see whatever seasonal decor Hogan’s has to offer.


Ender’s Falls

End your day with one more beautiful outdoor stop. Enders Falls is a short trail that includes views of multiple waterfalls. It’s located inside of Elders State Forest, offering 2,103 acres of forests, wetlands and waterfalls.

A waterfall cascading down rocks along a small stream in the forest.
Ender’s Falls

The Enders Brook loop trail is 1 mile and rated easy with 134 feet of elevation gain. You will take some steps down and get to walk right along Enders Brook. I saw 4 waterfalls in just over a half mile! This spot is free to visit and makes for the perfect quick stop to end your day.


More Things To Do in Connecticut

For more hikes in Connecticut and New England, my friend Kristen at Early Bird on the Trail has you covered! Check out her blog for many more Connecticut guides.

Some spots on my list for next time include:

  • Steep Rock Preserve
  • Mine Hill Preserve
  • People’s State Forest
  • Macedonia Brook State Park
  • Kent Falls State Park
  • Mount Tom Tower

Where to Stay in Connecticut

If you need a place to stay in Connecticut, Hartford is a great central location between these spots.

For a historic hotel in downtown Hartford, it’s worth looking at a stay in The Goodwin Hotel. This is great if you’re looking for something more luxurious.

For more affordable hotel stays with good value, check out the downtown Hartford Holiday Inn or the Marriott near the Hartford airport.

For a unique camping experience, check out the Lake Compounce Campground. They offer cabins, tipis and sites for RVs and tents.

Finally, for a romantic cottage close to Enders Falls, take a look at the Windy Top Cottage on Airbnb.


Final Thoughts

I hope this gives you some ideas for a quick trip to Connecticut. It’s a beautiful state that is underrated when it comes to outdoor adventure.

For more New England and New York Travel Guides, check out these blogs:

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