One of the most charming towns in northwest Connecticut is Kent, which is filled with stunning rural scenery, beautiful parks, gorgeous fall foliage, and so much charm around every corner. It’s such a dreamy destination for both day trips and cozy weekend getaways.
To help you plan your own trip, this guide is all about the best things to do in Kent, CT. Having visited this quaint town during different seasons, I’m excited to share all the fun things that I think are worth checking out while in town. As one of my own personal favorite places to visit in the Connecticut countryside, I can’t wait for you to experience for yourself, too.
And with that, let’s get into it!
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Fun Things To Do In Beautiful Kent, CT
1. Explore Kent Falls State Park
The top attraction in Kent is definitely Kent Falls State Park, and for good reason – it’s home to Connecticut’s tallest waterfall! This park is fairly small compared to some of the other parks in the region, however, it offers a lot of beautiful scenery in addition to the waterfall, and I highly recommend visiting.
The waterfall, which is about 250 feet tall, is a short walk from the parking area, and from there, you can admire it from ground-level, or walk the Kent Falls Steps Trail to see it from higher viewpoints. This trails is pretty short and requires climbing a lot of stairs, but definitely worth checking out.
Additionally while at the park, you can hike the Red and Yellow Loop Trail, which is just under a mile, and does have some incline, so it’ll get your blood flowing. You’ll enjoy different views of the waterfall here as well, and are also rewarded with some nice views of the town’s surrounding mountains.
Good To Know: This park charges an admission fee for out-of-state visitors, so you’ll want to plan accordingly. There’s not always a gate attendant there to collect your admission fee, so look for signs that tell you how to pay online. If your cell service isn’t letting you load the page (it can be slow out in this part of town), take a photo of the signs, and pay once you leave and have a better signal.
2. Explore The Charming Downtown
Kent is also home to a wonderful little downtown area with some great shops, restaurants, and cafés, so you’ll definitely want to budget at least an hour or so to explore this area.
One of my favorite parts of downtown Kent, though, is that you can admire some really lovely scenery just from Main Street, including beautiful buildings, lots of trees and greenery, and even mountain views. Lots of postcard-worthy moments can be found in this part of town!
Another cool feature of the downtown area is Kent Barns, which owns quite a few of the buildings in town that house local businesses, and about six of them are restored or re-built barns. This offers such a great architectural element to town, and adds to the overall feel and character when you visit.
While walking downtown, I really love to pop into Woodford’s General Store, House of Books (which I’ll talk more about in a minute 😉), Heron Shop, and Terston. But I have a few more suggestions I’ll get into later in this post!
3. Hit The Trails At Macedonia Brook State Park
While I love Kent Falls State Park, Macedonia Brook State Park is another fantastic place to explore that I can’t recommend enough. You’ll find a great mix of trails inside the park ranging in difficulty, including the more challenging hike up Cobble Mountain, which offers views of the Taconic and Catskills ranges.
But you can also enjoy some easier trails inside the park, as well as really nice views of the babbling brook (from which the park gets its name). If you’re really short on time, you can even just take a short drive through the park to get a sense of the scenery, and enjoy the views along the way.
Good To Know: Parking at this park is free for all visitors, so enjoy! I also really recommend making this park a priority if visiting in the fall season, as you’ll experience some pretty awesome foliage color in October.
4. Sip Local Beer At Kent Falls Brewing Company
Located about 15 minutes from downtown on a beautiful piece of land, Kent Falls Brewing is a really cool place to visit, especially if you love craft beer. As a working farm and brewery, you’ll enjoy gorgeous rural views when you arrive, and then cozy up in their tasting room to enjoy what’s on tap.
Good To Know: The tasting room is usually open Thursday through Sunday, and they offer up to 4 tastings per person during your visit to get a sense of which you like the most. You can also purchase cans and bottles to enjoy while you visit, and leashed dogs are allowed in their outdoor space!
5. Pop Into The 109 Cheese Market
One of the coolest specialty markets in downtown Kent is the 109 Cheese Market, but one of the reasons they’re worth a visit is because they also offer some really awesome classes throughout the year.
Not only do they have a wonderfully-curated selection of cheeses, wines, and speciality foods, their classes are a fun enhancement to your experience, on top of filling up your basket, of course. In the past, they’ve offered wine and cheese pairings, wine tastings, cooking classes, and more. This is definitely worth checking out to see if any of these experiences align with your visit!
Even if you’re not able to attend one of their classes or events, you can just swing by for a sandwich – the food here is so, so good, and their grilled cheese really hits the spot after a hike 😉 In fact, they’re known for having one of the best grilled cheese sandwiches in the area!
6. Dine At Kingsley Tavern
One of the best places for a meal out in Kent is Kingsley Tavern, which is a cozy little spot nestled right in the downtown area.
Serving dinner and brunch, their menu offers elevated comfort food and classic American fare. You’ll enjoy options to choose from including burgers, tacos, pasta, meatloaf, poutine, and so many more yummy menu items.
In season, they also have outdoor seating areas!
7. Find Your Next Great Read At House Of Books
I’m personally such a sucker for a great bookstore, and House of Books in downtown Kent is a really fun one to visit. Recently renovated, the interior still feels cozy and welcoming, but is also incredible easy and comfortable to navigate. They’ve done some very cool things with their merchandising, too, that creates a unique and memorable feel inside.
But not only that, the staff here is very friendly and helpful, so if you’re in need of a recommendation, don’t be shy! If you’re traveling with youngsters, they also have a wonderful children’s section.
8. Meander Through Kent Greenhouse & Gardens
Located just a few minutes from downtown, the Kent Greenhouse & Gardens is a nursery and market that’s definitely worth checking out. While a large part of it is, in fact, a garden center, they also have a nice little shop inside that sells unique home goods and finds, so there’s something for everyone here.
However, their outdoor nursery space is something you’ll likely enjoy, even if you’re not an avid gardener. The giant topiary archways that lead to the shop’s entrance offer such a whimsical design to the space, and you’ll find a variety of plants and flowers here to peruse, too.
If you’re not a plant-lover, then definitely make a note to stop by to shop their store inside, which has really cute gifts and home decor. I always seem to find something to buy when I’m here.
9. Pick Up All Kinds Of Goodies At 45 On Main: Coffee, Pastries & More!
When you’re looking for a little afternoon snack or a pick-me-up, 45 On Main is the place to go! They have an extensive drink menu that includes coffee, chai, matcha, lemonades, and refreshers. But they also have lots of delicious treats to pick from if you’re craving a little something sweet.
Inside the café is both cozy and quirky, and you’ll find selections of candies and chocolates, in addition to the café menu, too. In the fall, they also have cider donuts, but this place is so fun year-round. It’s my go-to for an afternoon drink and treat when I’m in town.
10. Enjoy A Relaxing Walk At Kent Land Trust
One of the more unique places to experience in town is the Kent Land Trust, which has really nice walking and hiking trails that are open to the public, as well as a community garden and public nature events throughout the year.
The Kent Land Trust protects over 2,300 acres of land in the area, and the trails system here is such a nice experience. The nature trails are relaxing and scenic, and this is a really fun place to check out when visiting.
Throughout the year, they also host guided hikes in the area, like winter animal tracking, so be sure to keep an eye out for those events when you visit.
Good To Know: Most trail systems within the Kent Land Trust are free to use and open to the public. However, since this organization is non-profit, I encourage you to make a cash donation when using the trails during your visit to support their community efforts, or you can easily make an online donation via PayPal by clicking here.
11. Hike Along The Appalachian Trail
The iconic Appalachian Trails runs through town, and for avid hikers, this is one of the best things to do in Kent when you visit! There are a few different options to hike the Appalachian Trail while in Kent, and here are some great options:
→ Bull’s Bridge to Ten Mile Hill
→ Schaghticoke Mountain via Appalachian Trail
→ Hoyt Road to Bulls Bridge
→ Caleb Peak via Appalachian Trail (most challenging)
12. Admire Bulls Covered Bridge
If you love looking for covered bridges, Kent is a great town to visit. Not only can you cross the Kent Falls Covered Bridge when visiting the park, you can also take a short drive to Bulls Covered Bridge.
Spanning just over 100 feet across the Housatonic River, Bulls Covered Bridge is easy to visit. There’s a small parking area just before getting to the bridge, so you’re able to walk over and admire the structure from different angles. Just keep in mind that this is a working bridge which sees its fair share of vehicle traffic, so be safe when visiting, and don’t block any cars trying to pass through.
13. Explore The Connecticut Antique Machinery Museum
This museum is such a cool experience to have, and definitely one of the best things to do in Kent when visiting.
The Connecticut Antique Machinery Association is a non-profit museum committed to preserving, restoring, and showcasing antique machinery that highlights the local industrial and agricultural heritage. Operated entirely by dedicated volunteers, they do a fantastic job bringing history to life.
The museum is largely outdoors, so this is one you’ll be better off visiting on a nice day. While exploring the grounds, you’ll enjoy historic machinery including a steam train, a working blacksmith, fire trucks, a schoolhouse building, and even a very cool rock museum.
Good To Know: The museum is free to visit, but if you enjoy your time here, I recommend making a donation to help them maintain the museum for years to come.
14. Visit The Eric Sloane Museum
For history lovers, the Eric Sloane Museum is a great way to learn about the local history in Kent. This museum is only open seasonally, usually May through October, but if you happen to visit during these months, it’s worth checking out.
Eric Sloane was a local Kent author, historian, and artist, and this space celebrates his life and work. Known for his passion for early American history and craftsmanship, Sloane’s legacy comes to life through exhibits of his paintings, illustrations, and tools. During your visit to the museum, you can explore a fascinating collection of antique tools and learn about early American agriculture. The museum also features a replica of a 19th-century workshop, which is one of the highlights during your visit.
Good To Know: There is an admission fee to enter the museum, so you’ll want to plan accordingly.
15. Hunt For Art & Antiques
If you love to look for antiques when you travel, Kent is a great place to do that. In addition to a great antique shop in town, there are also several art galleries to visit.
For antiques, RT Facts Design & Antiques is where to go in town, and the store is such a great space to explore. It’s merchandised really well, and they also have a lot of larger, unique pieces that are really fun to peruse.
I’m not an art connoisseur, and moreso just know what I personally enjoy, but not necessarily what’s exciting or noteworthy in the art world. However, I enjoy almost all the art galleries in Kent I’ve visited, and here are some of the ones I recommend that you check out during your stay:
→ Kent Art Association
→ Morrison Gallery (which feels a bit like a museum, but worth popping into!)
→ Ober Gallery
16. Celebrate Spring With Daffodil Days
Downtown Kent sees thousands of daffodils in bloom every spring season, which is such a fun time to visit! On a nice day, enjoy seeing these cheerful flowers emerge all over downtown, signaling that winter is over and warmer days are ahead.
While there’s no designated festival that I know of to celebrate the daffodil blooms, it’s still a great sight to see in the springtime, perfect for photos or just that little bit of cheer you need after a long winter season. Sidewalks and green spaces around the downtown area begin to come alive with bursts of yellow and white, making this such a lovely time to experience this already charming town.
17. Enjoy The Kent Gingerbread House Fest During The Holidays
Visiting during the holiday season? Then you’re in luck! Throughout December, the local shops downtown will host beautiful gingerbread houses to admire, and they also come with a little game to win prizes.
Maps of all the houses are provided, and each house also has a riddle to solve. If you find all the houses, and solve all the riddles, you can turn your map in for a prize! Maps are available at all gingerbread house locations.
Not a bad way to celebrate the holidays in this cozy New England town, am I right? 😉
Fun Fall Things To Do In & Around Kent, CT
Since Kent is home to some rather incredible fall foliage, this season is a popular one for visitors, and for that reason, I wanted to suggest some fun things to do in the area during this time of the year. Enjoy!
18. Have The Perfect Fall Day At Averill Farm
This beautiful farm is in Washington Depot, just 25 minutes from Kent, and worth every second of the drive to get there. A quintessential fall farm, Averill offers apple picking, cider, donuts, and fresh flowers grown on their land (in season), which means you can plan the perfect day of fall fun during your visit.
19. Head To Hogan’s Cider Mill
This one’s a bit further of a drive, but if you head out to visit Litchfield (which I talk about later in the post), it’s not too much further. Hogan’s Cider Mill has gotten a little Instagram-famous in the last few years, and deservedly so! Serving up creative and over-the-top cider drinks, topped with a full cider donut, it’s the perfect fall treat to enjoy while you savor the fall foliage in the area.
They do a great job updating their website and Facebook page during the fall season, so you’ll always have access to their hours and current drink specials. They do get pretty busy on weekends, so if you’re visiting during that time, plan accordingly.
20. Plan A Night At The Scarrybrooke Park Haunted Trail
Located in New Milford, the Scarrybrooke Haunted Trail is a lot of fun to plan the perfect spooky Halloween night out. Run entirely by volunteers, this haunted attraction will definitely give you all the goosebumps, so come ready to be scared!
Where To Stay In Kent, CT
The Kent Collection Firefly Inn & Garden Cottages: The top place to stay in town, and while it’s a splurge, it’s so nice if it’s within your budget! The Firefly Inn property is an idyllic New England colonial, and has been lovingly renovated to offer upscale but cozy accommodations. You can also choose to stay at the adorable garden cottages in the heart of downtown, but both properties are within walking distance to town.
→ Click here to check rates & availability at the Kent Collection
Awesome Things To Do Near Kent
Kent is absolutely beautiful, but since it’s located within the Litchfield Hills region of Connecticut, there are so many other great towns and things to check out nearby. Here’s what I also recommend adding to your Kent itinerary:
21. Take A Drive To Lovely Litchfield
One of the most picturesque towns in the area is Litchfield, and here, you’ll find a quaint downtown area, great nature trails to explore, a distillery, and wonderful restaurants. The downtown space feels like a New England postcard, and it’s only about 30 minutes from Kent.
Some of my favorite things to do in Litchfield are White Memorial Conservation Center, Topsmead State Forest, the White Flower Farm garden center, and Espresso 59 café. However, there are so many more things to do in this area of the Litchfield Hills, and one in particular is a great stop to make on your way from Kent (which is my next suggestion!).
Psst! I have an entire guide on the best things to do in Litchfield, CT, if you need more ideas 😉
22. Visit Thorncrest Farm & Milk House Chocolates On The Way
On your way to Litchfield, you’ll definitely want to stop in Goshen to visit Thorncrest Farm & Milk House Chocolates. Tucked away in the woods down a dirt road, this farm is such a treat to visit (literally!). Their hand-crafted chocolates are made using their own milk, and gosh, they’re so good, you guys.
Their menu of chocolates changes frequently, so when you walk into the chocolate house, be sure to look for the glass case that features that day’s selection. Before you leave, you can also pop into the dairy barn to see the cows.
23. Visit Adorable New Milford
Another wonderful town to visit in the area is New Milford, which is about 25 minutes from Kent. New Milford has a picturesque downtown area with shops, cafés, and restaurants, and nearby are also some nice parks to visit.
While here, you’ll likely spend the bulk of your time in the downtown area, which has a lovely town green and gazebo. But I also like to recommend you visit Lover’s Leap State Park, Park Lane Cider Mill, and Lynn Deming Park (if visiting off season because in-season admission is pretty hefty at this particular park).
Psst! I have an entire guide on the best things to do in New Milford, CT, if you need more suggestions 😉
24. Walk Or Drive Across West Cornwall Covered Bridge
The longest covered bridge in Connecticut is only about 20 minutes north, and worth checking out if you love New England’s covered bridges (like I do!).
This bridge is located in a more residential area, but there are a few parking spaces available so you’re able to get out of your car to explore and take photos. Much like Bulls Covered Bridge, this bridge is regularly used for traffic, so be careful while visiting and be sure to stay out of the way of oncoming cars.
25. See The Real Stars Hollow – Washington Depot
Lastly, about 25 minutes from Kent, you’ll find the quaint town of Washington Depot, which is widely-regarded as the real Stars Hollow from Gilmore Girls. If you’re a fan of the show, you’ll be excited to know that Amy Sherman-Palladino was staying at The Mayflower Inn in Washington while writing the pilot for the show. And in my humble opinion, I think this town truly is the closest to Stars Hollow of all the towns in the area.
However, if you’re not a fan of the show, you don’t have to have any clue what I’m taking about to enjoy visiting. While this is a very small town, it provides all the New England vibes you’re looking for. You’ll find cute cafés, a charming bookshop, a beautiful park to explore, and picturesque side streets for walking. There are some things to know before visiting, though, so I do highly recommend you click the link below to read my guide on Washington and Washington Depot.
Psst! I have an entire guide on what it’s like visiting the real Stars Hollow, which shares fun things to do in town, and why I think this is the true Stars Hollow experience 😉
Visiting Kent, CT FAQ
Is Kent, CT Worth Visiting?
100%! If you’re looking to escape to an authentic and idyllic rural town, Kent checks all the boxes. You’ll find a nice little downtown area with shops and restaurants, cozy cafés, scenic roads, beautiful parks, covered bridges, and quaint places to stay.
Does Kent, CT Have A Downtown?
It sure does! The downtown area is small, but has a nice mix of shops and eateries, as well as art galleries, green spaces, mountain scenery you can admire the sidewalks, and is very walkable. Keep in mind, though, it is along the main road through town, so you’ll experience some street noise. However, the overall charm of the area more than makes up for that 😉
What’s The Best Time Of Year To Visit Kent?
Personally, I really love the fall season in Kent, which is one of the most popular times to visit because of the stunning fall foliage displays around this area. However, each season in Kent offers something different, and spring during daffodil season, summer sunshine, and winter serenity are all wonderful to experience in Kent, too.
Psst! I have a guide on Fall in Connecticut, which features my favorite fall foliage towns, things to do, and more.
Is Kent, CT Walkable?
Downtown Kent is walkable when visiting the clusters of shops and such, however, you’ll need to drive to most of the other attractions in town.
How Many Days Do You Need In Kent?
Kent is very small, and you can easily see a lot of it in a day. However, if you’re looking for a slower-paced getaway, want more time to explore a lot of the parks and hiking trails nearby, or are simply using Kent as a home base for exploring the Litchfield Hills region, a long weekend (2-3 days) is also perfect.
That’s A Wrap On Awesome Things To Do In Kent, CT!
And there you have it! Now that you’ve got the inside scoop on all the most fun things to do in Kent, CT, and the surrounding areas, you’re ready to plan your own cozy little getaway. Kent is really hard to beat if you’re looking for beautiful countryside views, small town life, cozy inns and cafés, quaint shops, and lots of outdoors space to explore. Happy planning!
