Top 24 Fun & Adventurous Things to Do in Kent, CT

From the best hikes in CT to a famous restaurant featured in the NYT, art galleries, the Appalachian Trail, and more! You’ll find 24 fun things to do in Kent, CT, where you can combine adventure, top-notch food, unique shops, galleries, and museums!

man on pine knob loop trail hike in early fall in connecticut
kent falls waterfall in winter

I’ve lived in Connecticut all my life aside from a brief stint in the Berkshires so I know my way around and am happy to bring you this long list of activities in Kent to choose from.

If you’re like me a day trip somewhere must include a hike or walk before or after popping into fun shops and cafes. I’ll drive over an hour for a cute town, a good view and a latte! And if you’re looking for any of this you’ll find it all in the quaint town of Kent.

shopping & restaurants downtown kent in winter
hike up cobble mountain at macedonia brook park in kent connecticut

Since the Appalachian Trail runs through Kent, you’ll find plenty of hikes and trails here. But if you’re not much of a hiker or visiting with someone in regular old Sketchers, you can still enjoy a walk in town, drive through CT’s longest covered bridge, view the tallest waterfall, and get an amazing meal.

Create the perfect day or weekend trip to Kent with this list of activities!

So let’s get to it, friends!

24 Fun & Adventurous Things to Do in Kent, CT!

1. Take a ride through Connecticut’s longest-covered bridge!

connecticut cornwall covered bridge in fall
west cornwall covered bridge in fall
Park area along the bridge for you to sit & take in the scene!

Running 172 feet over the Housatonic River, you’ll find this bridge in West Cornwall (just 14 minutes from Kent!) where the Sharon-Goshen Turnpike (Rt 128) meets Route 7.

But don’t all rush there at once! 😱 This is a covered bridge you drive through, one car at a time. And there are places to park and walk around the little park along the river, bench included.

2. Take a ride through Bull’s Bridge

A covered bridge, historic landmark in Kent, and a waterfall! Bull’s Bridge has it all and it does get crowded here in fall so plan accordingly!

Built in 1842, Bulls Bridge is one of the few functional covered bridges remaining in Connecticut. There is a free lot where you park and a short walk to this scenic wooden bridge along with waterfalls, rapids, overviews, a small gorge, and hiking trails (Appalachian Trail) just beyond the bridge!

3. Kent Falls – Connecticut’s Tallest Waterfall!

connecticut's tallest waterfall kent falls in winter
The falls in late spring
kent falls in winter
A portion of the falls in winter

If visiting Kent, a stop at Kent Falls, the tallest waterfall in Connecticut, is a must! And you hardly have to take any steps to see it.

You view this 250 ft tall waterfall from the comfort of your car or you can walk just several hundred feet on a flat paved path to the base of the falls. And if you’re up for exploring more you can walk the path to the right of Kent Falls up several sets of stairs that lead to several viewing platforms each at a different level of this tall fall.

4. Kent Falls Brewing

I haven’t been here yet but if you’re visiting Kent and are a fan of local beer check them out!

As a farm brewery, our surroundings and experiences inform much of what we do. We aim to produce beer reflective of the land around us, the people that occupy it and the culture we wish to promote.

The brewery sits on, and is a part of Camps Road Farm; a 50 acre diversified farm in Kent, CT. The farm focuses on pasture-raised poultry and pork, along with our 1 acre of hops and acre and a half of cider apples destined for Neversink Spirits, our distillery located in Port Chester, NY.

5. Kingsley Tavern

I don’t want to put too much pressure on the place but I had the best meal of my life (or in a long time!) at Kingsley Tavern right along Main Street in Kent.

Don’t just take my word for it – they were also featured in and got a great review in the New York Times!

dinner at kingsley tavern in kent ct
I got the curry stew with chickpeas, oh my goodness, I keep dreaming about it & want to go back!!
dinner at kingsley tavern in kent ct
Our cozy corner table…🍷🍺

6. 45 on Main Coffee, Chocolate, and Creamery

This is a must-stop shop when visiting in Kent! I love stopping here for a coffee or hot chocolate after a hike. And then the treats! All kinds of homemade baked goods and chocolates.

Indulgence is our specialty, and we take pride in offering a tempting selection of homemade cakes and chocolates. Each delectable treat is lovingly crafted using the finest ingredients, ensuring every bite is a moment of pure bliss. From moist cakes to melt-in-your-mouth truffles, our creations are a testament to our dedication to quality and taste. yum!

45 on main cafe chocolates in kent ct
45 on main in kent ct

7. Check out one of Kent’s four art galleries in town! ⬇️ 🎨🖼

After picking up your latte at 45 on Main stroll along Main Street and pop into one of the galleries below to admire the local talent!

8. Local Shops

shopping & restaurants downtown kent in winter
Love the downtown shops in Kent!
shopping & restaurants downtown kent in winter

Hikes & Trails in Kent, Connecticut

9. Kent Land Trust

kent land trust in winter with view of housatonic river
kent land trust in winter with red barn
dog at skiff mountain preserve kent connecticut

Take your pick from 10 different trails ranging from 0.2 – 2.8 miles. There’s nothing technical or difficult about the trails in Kent Land Trust but I love how several of them hug right along the Housatonic River.

Click the link here to check out the map and pick your trail!

10. Macedonia Brook State Park in Kent, Cobble Mountain

view from top of cobble mountain in kent ct

Click the link above and take your pick from 5 different trails in this beautiful state park in Kent. The shortest route up to Cobble Mountain is 2.2 miles and longest is 6.8.

Even if you’re not a hiker I suggest still visiting this park taking a ride down Macedonia Brook Road which runs right alongside (of course) Macedonia Brook.

11. Pond Mountain and Fuller Pond Loop

hike around pond mountain in kent ct in spring
dog and man walking up pond mountain in kent ct

Enjoy this 3 mile loop that takes you right alongside Fuller Pond and then up to Pond Mountain!

This is a moderate hike with about 613 feet of elevation gain but I think it’s worth it! I love the view from the top of Pond Mountain as well as the views of Fuller Pond as you walk around it.

12. Caleb’s Peak on the Appalachian Trail

woman on hike at caleb's peak in kent ct in spring
appalachian trail view at calebs peak

If you’re up for a BIG hike in Kent then look no further than this 8.9 mile hike with 2,600 feet of elevation gain! This hike is labeled ‘Hard’ on AllTrails.

This hike combines the views from Caleb’s Peak as well as St. John’s Ledges. Complete this one and you’ll have hiked several miles of the 2,190 mile long Appalachian Trail!

13. St John’s Ledges on the Appalachian Trail

Hiking St Johns Ledges on the Appalachian Trail; A Guide
Woman sitting on mountain top sipping water with brown mountains in distance

Another Appalachian Trail hike right in Kent! I wrote a whole post on 3 different routes you can take to see the views from St John’s Ledges.

These hikes range from 2 miles to over 8 but all combine the vertical rock slabs of St Johns Ledges. The view from here faces east which would be great for sunrise!

14. Numeral Rock

black dog on sunrise hike at numeral rock in kent ct
Captain looking out at sunrise over the town of Kent saying Wake up! 🐶
sunrise hike at numeral rock in kent ct

Enjoy a short hike to a peak overlooking downtown Kent! We hiked here for sunrise and I loved being able to spot the white steeple from St Andrew’s Church.

This is also known as “graffiti rock” since every year the students at the Kent School hike up and spray paint their graduating year (and sometimes other things like names) at the top. This part I didn’t like but I think the short walk and view is definitely worth it!

15. Pine Knob Loop Trail

woman at top of pine knob loop hike with green mountain view early fall
nobody mind me, I just have the tag still on my LL Bean shirt 👀
hatch brook falls pine knob loop trail
So many little falls and pools here! Great for the dogs to get water

This is a favorite hike of mine in Connecticut and how lucky that it is right outside of Kent! If visiting Kent and looking for a beautiful mountain lookout then choose this hike!

This hike packs a lot into its 2.5 miles from the walk all along Hatch Brook Falls to 2 big views at the top of Pine Knob. This is a view that faces east and can be a little steep but appropriate for an intermediate or advanced beginner hiker.

16. Lake Waramaug Trail

woman smiling with dog at lake waramaug in connecticut
hike near kent connecticut in summer with green grass and sun shining

If looking for a short hike to do near Kent with big views, then look no further than Waramaug’s Trail!

While this trail is only 1.6 miles round trip it does have almost 500 feet of elevation so it is STEEP! Perfect for an intermediate or advanced beginner hiker. Enjoy the views of Lake Waramaug and even hike up to watch the sunset as this view faces west!

17. Housatonic River Wildlife Management Area

Housatonic river management area kent ct winter walk
winter walk at housatonic river management area kent ct

If you’re looking for a flat path to walk for 5 minutes or 30 while along the peaceful Housatonic River then check out the Housatonic River Wildlife Management area in Kent!

I love how this site put it: “Step foot into the Housatonic River Wildlife Management Area, and you’ll be greeted by the harmonious symphony of nature—a place where wildlife thrives and nature rejuvenates. This protected habitat is home to a diverse range of species, both flora and fauna, creating a vibrant ecosystem that reflects the beauty of untouched nature.”

18. Ski or Hike at Mohawk Mountain!

If visiting in winter check out Connecticut’s premier ski mountain that offers skiing, lessons, rentals, and tubing!

Or, if it’s not winter you can take the 4-mile (round trip) hike to the top of Mohawk Mountain or you can even drive up to the top to check out the view. There are almost 360 degree views here with benches to sit and relax and take in the view!

19. Covered Bridge Electric Bike

Don’t like to hike?! How about an E-bike? What a fun way to see the town of Kent. I haven’t done this yet but if and when I do – I would take it down some of the more rural roads to enjoy the country views and homes in Kent

20. Connecticut Museum of Mining and Mineral Science

The Connecticut Antique Machinery Association states on their website that the main focus is to “educate the general public as to early industrial and agricultural methods”. So if you are visiting Kent and like history and want to check out antique machinery from CT’s agricultural past then make a stop here!

CAMA is a living museum meaning that most of its exhibits are operable! 

21. The Institute for American Indian Studies Museum and Research Center

I haven’t been here yet but drive by all the time on my way to or from Kent and I keep saying that I have to stop in.

“IAIS preserves and educates through discovery and creativity the diverse traditions, vitality and knowledge of Native American Cultures.”

The museum was started in 1975 as an outgrowth of local efforts to recover New England’s then-largely-unknown indigenous history. The museum and research center dedicated to providing unique, informative and engaging experiences for our members and visitors alike.

22. Visit the Kent Historical Society

Take a tour through the history of Kent!

The prized possession of the Kent Historical Society is our museum house, Seven Hearths (located at 4 Studio Hill Road), which is open for tours by appointment. This a large pre-Revolutionary house circa 1751. As the flagship of the Flanders National Historic District, and the only original building open to the public, Seven Hearths offers a unique view of the early development of the Town of Kent. For much of the twentieth century it was the home and studio of noted New York artist George Laurence Nelson.

23. Kent Yoga & Bodyworks

Staying in Kent for multiple days?! Then maybe you want to stay regular with your yoga routine! Take a class here or even treat yourself to a massage.

24. Hopkins Vineyard

If you like incorporating a vineyard into your weekend stays then take the 17-minute ride to the dog-friendly and scenic Hopkins Vineyard in Warren, CT.

The vineyard is a National Bicentennial farm owned and run by the Hopkins Family for over 235 years. Check their website for hours and events and plan your visit!

I hope you enjoyed this list of the best things to do in Kent, CT!

If you need a place to stay while in the area check out my post of the 10 best inns in Litchfield County! (Pet-friendly, too) With one inn right in downtown Kent! ⬇️🏠

And for another fun day, check out my post all about a fun day trip to Newtown, Connecticut which is filled with things to do & see! 🥾☕️

southford falls waterfall near newtown connecticut

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  1. I’ve never been to Kent Connecticut but now I want to. Kent Falls looks absolutely beautiful and I’d love to explore all those shops on a weekend there!

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