Things to Do in Kent, CT: 15 of the Most Unique

If you’re ready to live out your Stars Hollow dreams, Kent, Connecticut, is the town for you.

I mean, there’s really no bad time of year to visit Kent, CT, but there’s truly something magical in the air during the fall here.

From pumpkins scattered on front porches, the orange and red hues of trees, and the quaintness of the shops and town squares, it’s truly unmatched. And who’s not trying to live their Lorelai Gilmore moment?

That said, Kent also really comes alive during the summer. The trees become vibrant shades of green, and the hiking trails are so gorgeous, overlooking lakes and rivers, you’ll want to set up a camp and stay forever.

Want to learn more about the gorgeous town of Kent, CT? Keep reading!

Map design by Stanton House Inn with elements from Flaticon

Top Things to do in Kent CT

Kent, founded in 1739, has a long history as a farming community and thriving producer of iron ore. It is now a rural community of approximately 3,000 people. Like most New England towns, it has numerous small hamlets such as Bulls Bridge, Kent Hollow, South Kent, and The Cobble. Kent is primarily a residential community with a small amount of industry and farming. That said, the downtown area has become a popular day trip destination.

Main Street and Downtown Kent

At risk of sounding like a cliche, I love Kent! And considering how close it is to the New York border, lots of people from NYC and nearby cities make day trips up here. The busiest period stretches from:

August, when the towns of the Litchfield Hills are cooler than elsewhere
Up to October, where it and nearby towns are the perfect place to see CT fall foliage

Route 7, stretching from Norwalk, CT up to the Massachusetts border and beyond, passes through the center of Kent. It’s a personal favorite of fall foliage driving routes.

While there are some side streets, the main drag is where you’ll find most of the shops, art galleries, and restaurants. Don’t miss the old train station converted into a pharmacy for one of Kent’s most unique attractions. Walking or biking around downtown to peak in people’s gardens is also a charming introduction to this classic New England town.

A few top ones to visit include:

Kent Coffee & Chocolate

Kent Coffee & Chocolate is a cute coffee and chocolate shop in Kent that offers a wide variety of gourmet coffees, teas, and sweets! This is the place to go if you need a quick cup of coffee or if you have a sweet tooth in need of a delicious freshly baked treat. Kent Coffee & Chocolate is also a great place to pick up cute souvenirs.

House of Books

The House of Books, which first opened its doors in 1976, is an upscale bookstore conveniently located right on Main Street. The shop is inside a historic building that was built to serve as a public library and is still the town’s most important literary landmark to this day. Aside from high-quality fiction and non-fiction books, the store sells:

Greeting cards
Gifts
And stationary supplies

Visitors will also find historical information about the area. The extensive collection of trail guides and local maps make it an excellent stop before hiking the local part of the Appalachian Trail.

Fife ‘n Drum Restaurant

The Fife ‘n Drum Restaurant has been proudly family owned and operated since 1973. The food is prepared using as many locally sourced ingredients as possible, and the menu is constantly changing to reflect what is in season. Menu items are vegetarian, vegan, and gluten-free. Except for Tuesdays, the restaurant is open every day of the week. You’ll find live music here four days a week, with special performances on Fridays.

Villager Restaurant & Catering

Villager Restaurant & Catering is the only restaurant in town that serves breakfast. This cozy, family-friendly restaurant has a diverse menu of traditional Mexican dishes and classic American favorites. Many of the breakfast items include free tea or coffee, and the lunch specials and soups change daily. Every day of the week, the restaurant serves breakfast, brunch, and lunch. Come for their special dinners on Tuesdays during the summer and fall.

Gallery at Kent Art Association

The Gallery at the Kent Art Association was founded in 1923 by a group of nine artists from New York who had moved to Kent to settle down. Among these artists were Williard Dryden Paddock, Spencer Nichols, and Frederick Waugh. Their goal was to provide a home for both emerging and established artists. The non-profit also works to promote the development and cultivation of art appreciation in Kent. The gallery building was completed by 1956. It now houses a beautiful collection of mixed medium art by their growing number of represented artists.

Hiking trails near Kent, Connecticut

Hikes, hikes, and more hikes. Seriously, if you’re someone who loves a good scenic trail or outdoor activities, the town of Kent has some of the best in the area.

And if you’re not much of a hiker, don’t be discouraged from trying out some trails! They can be as relaxed or intense as you’d like them to be.

The Kent Land Trust maintains a fantastic system of trails. The non profit hosts public hikes throughout the year, plus community gardens just outside the center of town.

Bulls Bridge

This spot is just downright gorgeous. It’s a pretty even terrain, so it’s welcoming to everything, but what makes it really special is the view.

Bulls Bridge is one of three remaining covered bridges still standing in Connecticut from the 19th-century. In 1781, George Washington crossed the Housatonic River near the current bridge. This single-lane covered bridge with a lattice truss design was built in 1842 by architect Ithiel Town.

You’ll walk under a historic covered bridge and then emerge, overlooking a gorgeous stream. Walk a little further, and you’ll be able to enjoy the soft sounds and lovely scenery of gentle rapids. Who doesn’t love a little waterfall?

Kent Hollow

For a wonderful valley hike, Kent Hollow is situated in the Appalachian Mountains in the upper reaches of the West Aspetuck River. Fun Fact: This is one of the cleanest rivers in Southern New England and itself classified as AA water quality.

The Hollow has four rolling and historic farms on its land, including Anderson, DeVaux, Rehnberg, and Wilsea.

It also has the Kent Hollow Cemetery if you love the quiet and being able to learn about some of the town’s community members. It might sound depressing, but grabbing a book and resting at a cemetery is truly serene.

Kent Falls State Park

If you’re looking for a place that’s serenity through and through, this is the spot for you.

With rolling streams and lush grasses, your walk or hike will be so relaxing it won’t even feel like a workout.

Kent Falls State Park is just off the highway for those looking for the simplest option. It’s equipped with picnic tables and benches so you can sit a spell with your family and enjoy a picnic.

For those up for a mile-long trip around, the falls are a great option and almost one you can’t miss. And while the main trail up Kent Falls State Park is normally packed, the side trails or extensions into the surrounding woods are typically much quieter. Nothing says New England quite like its incredible nature!

Macedonia Brook State Park

Macedonia Brook State Park is unmissable if you enjoy a hike during the fall with colorful leaves and the crunching sound under your feet. You walk along a stunning lake home to many birds and wildlife for spotting enthusiasts.

The trails on the east side of the road are not as steep for those not ready for anything too intense. There are still some elevation changes but nothing too crazy.

If you stick to the Red Trail, you’ll remain along the brook for the most stunning view. It just makes me want to grab a book or a set of paints and spend the afternoon taking in the scenery.

Hike the Blue Trail across Cobble Mountain and other peaks for spectacular views of the Catskill and Taconic mountains, which are beautiful in the fall.

Appalachian Trail

From the Soldier’s Monument at the corner of Bridge Street and Main Street, walk along Bridge Street towards the Housatonic River. Cross the river, pass Kent School, and eventually you’ll see a trail crossing Route 341.

This trail is the Appalachian Trail, stretching from the mountains of Georgia up to Maine. I’m a fan of walking portions of it in every state I visit.

If you’re looking to do the same while you’re here, you’re welcome.

Don’t Miss the Museums in Kent, Connecticut

Museums in New England are so special, as these are some of the oldest (founded) states in America! There’s a rich history here to learn, and the best part about museums is that you get to see some of the United States’ oldest history up close and personal.

This small town has hosted more than a few visionaries:

A former tribal chairwoman and cultural leader
A Supreme Court Justice
A Pulitzer Prize winning writer
A founding member of the Blue Öyster Cult
And various members of TV, movies, and music; many as students at local private schools like Kent School

So of course there are a few history museums worth visiting. A few are even on the National Register of Historic Places.

Connecticut Antique Machinery Association

At the Connecticut Antique Machinery Association, you’ll see some very old, very large machinery used throughout decades of American farming, including tractors and steam shovels.

Over at the mining museum on the grounds, you’ll get to see some of New England’s gorgeous and very old land gems. While there are plaques around offering information about all the artifacts, there are also volunteers happy to walk through the non profit museum. They’ll explain where everything is from, including where the rocks, crystals & quartz were mined.

If you want to bring home some memorabilia, there’s a small gift shop where you can grab a mug or shirt. They also accept donations if you’re fine skipping on a souvenir.

In September, they even hold an annual festival that’s great for families from the 22nd to 24th. You’ll be able to check out demonstrations, added steam engines, and the running of the Nagle-Corliss engine, among other antique machinery.

The Eric Sloane Museum & Kent Furnace

The Eric Sloane Museum has some of the earliest American tools—and we’re talking old. It’s also the site of the Kent Iron Furnace, and if you don’t know, it began production of pig iron in 1826.

The hand tools at the Sloane-Stanley museum will make you grateful for the technology we have today. We can only imagine how heavy these early American tools are. Especially those clippers!

Now who is Eric Sloane? Well, he lived on the grounds as a scientist, artist, and writer. He poured his life back into his country in all forms of art and practical gifts, from farm apparatuses to original paintings.

You Can’t Miss the Breweries!

Nothing goes hand in hand quite like a hike and a beer, am I right?

Kent has a phenomenal brewery, and there are a few others nearby.

Kent Falls Brewing

This farm brewery is so relaxing with wonderful beer, so grab some games and friends and spend the afternoon with your buddies.

Sitting on 50 acres, Kent Falls Brewery focuses on their pasture-raised poultry and pork. They even have an acre of hops and another acre and a half of cider apples. Basically, you can’t miss trying their hard cider while visiting!

At their tasting room, they love when visitors can check out their farm and learn more about their operations—all while sipping on beer. What more could you need?

Some other notable mentions not in Kent but nearby:

Special events in Kent

Not that you necessarily need another reason to visit Kent. But just in case:

Kent Memorial Library Book Sale

The Kent Memorial Library hosts their annual summer-long book sale on weekends from Memorial Day to early October. You never know what you’ll find, with bargains and one-of-a-kind finds such as:

Bestsellers
Mysteries
Biographies
And art history

Volunteers organize books by category that cater to all interests. I’ve usually go to eye their vintage and antique books for sale.

Places to Stay in Kent, CT

Kent makes a fantastic CT day trip. The drive from our Greenwich, Connecticut, bed and breakfast to Kent is about an hour and 20 minutes along gorgeous Route 7. It’s especially beautiful as a CT fall foliage driving route. But if you want to stay around a little longer and explore more of the area, you have plenty of charming options. Most of your options for places to stay in and near Kent are bed and breakfasts.

With one major exception.

Bed and Breakfasts in Kent, Connecticut

Experience the charming appeal of Kent, CT with its lovely bed and breakfast choices. Immerse yourself in the authentic charm of the area by staying at a quintessential Kent bed and breakfast. Experience the warm and comfortable atmosphere of these accommodations. The staff provides personalized service and pays great attention to detail. Wake up to the aroma of freshly brewed coffee and savor a delicious homemade breakfast, prepared with local ingredients. In Kent, the bed and breakfasts have historic architecture and lush gardens for an immersive experience.

The Kent Collection

The Kent Collection is happy to host you in three newly renovated places: The Victorian, Firefly Inn, and The Garden Cottages. The Victorian was built in 1890 and renovated in 2022. It offers large, fancy rooms and suites for family get-togethers, weekends, and special events. The Firefly was renovated and redecorated, but still has the cozy and welcoming vibe. Peter Starbuck owned it as a B&B for 20 years. The Garden Cottages, each with its own kitchen and private garden, vary in size and layout but share an eclectic, casual, cozy atmosphere. These accommodations are great for a relaxing getaway with family, and they’re close to town activities.

The Fife ‘n Drum Country Inn

The Fife ‘n Drum Country Inn provides overnight accommodations in the heart of town. The Inn, across from the Kent Green, is within walking distance of all the local shops and galleries. So you can eat well and then stay the night! That said, due to its prime location, it fills up well in advance.

Hotels in Kent, CT

Nearby to Kent is one of the most famous luxury hotels in Connecticut. Though if you want to stay in the lap of luxury, you’ll be paying with an arm and a leg.

Mayflower Inn & Spa

Relax in luxury at Mayflower Inn & Spa, one of Kent’s best hotels. It combines comfort and sophistication. Returning to your hotel is a treat, whether you’re exploring cultural offerings or embarking on adventures. Enjoy excellent service, beautiful rooms, and stunning views that change with the seasons.

Your journey to this New England gem promises relaxation, adventure, and a genuine connection to the town of Kent, CT.

Check Out So Much More in Litchfield County

While Kent has many amazing things to check out, Connecticut is a small state, so traveling around will only take a couple days. It’s worth venturing out and seeing everything the state has to offer!

Lakes on Lakes

For one, Connecticut lakes, like Lake Waramaug, are truly stunning. They all line the Connecticut River, so if you just drive along Route 3, you’ll be sure to hit them.

The lakes are great for hikes, picnics, and swimming—you name it, they’re fitting. Just be sure that if you want to swim, you go to the designated areas!

Learn More About Litchfield

Litchfield, CT, has such a rich history with gorgeous nature and adorable villages. There’s so much to do here, so be sure to check out our guide to the Litchfield Hills area of northwestern Connecticut.

And Kent, Connecticut is just one of many charming towns in Connecticut.

Check out our list of cute places to visit for day trips in Connecticut.

And be sure to read our full guide to the most unique places to visit, attractions, and activities across Connecticut.

Things to Do in Kent, CT: Small Town New England Charm