Things to Do in Kent, Connecticut: Hiking, Restaurants & Local Attractions
Updated: Nov 5
If you are staring at a map trying to piece together the perfect weekend escape, let me save you hours of research. Tucked into the northwest corner of Connecticut, right against the New York border, is the beautiful town of Kent.
Living just down the road in Litchfield County, I find myself driving out here constantly. Kent is hands-down one of the best hiking towns in Connecticut. It delivers over 30 miles of trails (including the Appalachian Trail) paired perfectly with a walkable village full of iced coffee, great pizza, and local shops to hit when your legs are tired.
Whether you are driving up from the city or looking for a quick Litchfield County day trip, here is exactly how to spend your time exploring Kent.
Beyond the Trails: Covered Bridges & Local History
Where to Eat & Drink After a Hike in Kent, CT
Local Shops, Galleries & Stops in Kent
Where to Stay Near Kent, CT
Best Time of Year to Visit Kent
Can You Do Kent, CT as a Day Trip?
Frequently Asked Questions
Why Kent Is One of Connecticut’s Best Hiking Towns
Kent is an outdoor lover's playground. You get access to spots like Kent Falls and Macedonia Brook State Park, plus multiple entry points to the Appalachian Trail.
What makes it so special is the logistics. You don't have to choose between a remote wilderness experience and comfort. You can hike a steep summit in the morning and be sitting in a walkable village eating a post-hike meal by noon. Because of its location, it is an incredibly easy day trip from New York, Western Massachusetts, and the rest of Connecticut.
Best Hikes in Kent, Connecticut
This town has trails for every energy level, from flat waterfall strolls to steep scrambles. Here are the best spots you need to know about, complete with all the trail logistics you need before you head out.
Kent Falls State Park
Exact Trail Name: Kent Falls Red & Yellow Loop Trail
Distance: 0.9-mile loop
Elevation Gain: Around 250 feet
Difficulty: Easy
Estimated Time: 30 to 45 minutes
Trailhead & Parking: Main parking lot directly off Route 7 in Kent, CT
Terrain: Paved stone stairs on one side of the falls, transitioning to a dirt and woodland path on the loop return.
What Makes It Worthwhile: You can walk right up to this 250-foot cascading waterfall straight from the parking lot.
Choose your own adventure: take the stairs up to the top of the falls to watch the water roar down, or follow the dirt path up through the woods for a quieter forest walk.
Dog Restrictions: Dogs are allowed on leash, but be cautious on the steep stone staircases when they are crowded or wet.
Seasonal Considerations: The mist freezes during winter, making the stone stairs and trails incredibly slick and icy. Microspikes are an absolute necessity if you visit in the colder months. Additionally, the parking lot hits capacity very early on weekends during the fall foliage season, so aim to arrive before 9 AM.
Macedonia Brook State Park
Exact Trail Name: Cobble Mountain Trail
Distance: Roughly 2.2-mile out and back
Elevation Gain: Around 730 feet
Difficulty: Moderate to Hard
Trailhead & Parking: Macedonia Brook State Park parking area off Macedonia Brook Road
Terrain: Rocky dirt paths, steep inclines, may require some scrambling.
What Makes It Worthwhile: If you want options, come here. The park has a ton of trails so you can easily mix and match your mileage, but the crown jewel is Cobble Mountain. The trail is steep and short, featuring fun, rocky sections that reward you with sweeping lookouts over the Harlem Valley.
Dog Restrictions: Dogs are welcome on leash, though the rocky scrambles require sure footing.
Seasonal Considerations: Fall foliage makes the exposed rock lookouts exceptionally scenic, but damp autumn leaves over steep granite can create slippery conditions.
Caleb’s Peak
Exact Trail Name: Appalachian Trail to Caleb’s Peak
Distance: Around 4.4 miles out and back
Elevation Gain: Approximately 600 feet
Difficulty: Moderate
Trailhead & Parking: Pond Mountain Natural Area on Fuller Mountain Road
Terrain: Forested dirt paths, connecting woodland tracks, rocky Appalachian Trail sections, and peaceful lakeside walking around the water.
What Makes It Worthwhile: This route offers a combination of varied terrain. Instead of a straight out and back, linking Caleb's Peak with the Fuller Pond area gives you both a rewarding summit viewpoint and tranquil water scenery. You will climb up to the open rock ledge at Caleb’s Peak for views over the Housatonic River Valley, then transition onto quiet forest paths that loop past the crystal clear waters of Fuller Pond.
Dog Restrictions: Dogs are permitted on leash.
Seasonal Considerations: The loop is exceptionally beautiful during the autumn months when the tree tunneled paths leading to Fuller Pond drop a canopy of colorful leaves. Spring can bring wet, muddy conditions along the shoreline sections, so proper footwear is recommended.
Pond Mountain
Exact Trail Name: Pond Mountain Natural Area and Fuller Pond Loop
Distance: Roughly 1.5 to 3 miles depending on whether you add the mountain ridge trails
Elevation Gain: Minimal around the pond loop, with roughly 400 feet if you hike the ascent
Difficulty: Easy to moderate
Trailhead & Parking: Grass parking area off Fuller Mountain Road (accessed via Route 341 and Macedonia Brook Road)
Terrain: Dirt forest paths, flat shoreline walking around the water, and optional steady ridge climbs.
What Makes It Worthwhile: Between Skiff Mountain and Macedonia State Park, this protected trust property is a dream when you want to escape heavy crowds. You can take the flat, peaceful loop that hugs the shoreline of Fuller Pond or hike to the lookout.
Dog Restrictions: Dogs are allowed on leash.
Seasonal Considerations: The flat pond loop is wonderful for a relaxed, quiet walk during spring and summer, while the property is beautiful during peak autumn foliage when you want to be away from the packed state parks.
Beyond the Trails: Covered Bridges & Local History
Bulls Covered Bridge
You cannot visit Kent without stopping here. Built in 1842, Bulls Bridge is one of the few functional covered bridges remaining in Connecticut. It spans the Housatonic River and is incredibly photogenic. There is a free parking lot and a short walk to view the wooden bridge, rapids, and a small gorge.
Bonus: You can hop right onto the Appalachian Trail from here.
Where to Eat & Drink After a Hike in Kent, CT
There is no hunger like post-hike hunger. Skip the guessing and head to these local favorites, complete with all the planning details you need.
Kent Falls Brewing Company
Address: 33 Camps Road, Kent, CT
Price Range: Moderate ($$ - craft pours and cans)
Current Operating Days: Open Thursday and Friday from 2 PM to 7 PM, and Saturday through Sunday from 1 PM to 6 PM (closed Monday through Wednesday).
Reservations: Not required; open seating in the tasting room and outdoor farm grounds.
Post-Hike Suitability: Perfect for a casual, highly relaxed post-hike reward. You can show up straight from the trail, grab a local craft beer in their 50 acre working farm brewery tasting room, and look out over the rural Litchfield County landscape.
Fife & Drum Restaurant and Inn
Address: 53 Main Street, Kent, CT
Price Range: Moderate to Upscale ($$ to $$$)
Current Operating Days: Open Monday and Friday from 1 PM to 8:30 PM, Wednesday and Thursday from 3 PM to 8:30 PM, and Saturday through Sunday from 12 PM to 8:30 PM (closed Tuesdays).
Reservations: Recommended for weekend dinners or indoor dining, though walk ins are often welcomed.
Post-Hike Suitability: This is a historic, classic Kent staple. It is best saved for after you have cleaned up and changed out of your hiking gear if you want a proper sit down, hearty, and slightly more upscale meal.
45onMain Coffee, Chocolate and Creamery
Address: 45 North Main Street, Kent, CT
Price Range: Inexpensive ($)
Current Operating Days: Open daily for morning and afternoon hours.
Reservations: Not needed.
Post-Hike Suitability: Highly convenient for a quick post-hike turnaround. This is your go to spot for specialty coffee, artisan chocolates, ice cream, and a fast hit of caffeine immediately after a hike.
The Villager Restaurant
Address: 28 North Main Street, Kent, CT
Price Range: Inexpensive to Moderate ($ to $$)
Current Operating Days: Open Tuesday through Sunday for breakfast, lunch, and select dinner hours (closed Mondays).
Reservations: Not required; casual walk in counter and table service.
Post-Hike Suitability: A staple for classic comfort food. If you finish a morning trek craving a massive, hearty diner style breakfast or a classic post-hike lunch right on Main Street, this is where you go.
Kent Pizza Garden (KPG Kitchen & Bar)
Address: 17 Railroad Street, Kent, CT
Price Range: Inexpensive to Moderate ($ to $$)
Current Operating Days: Open daily for lunch and dinner service.
Reservations: Not required; casual counter service and dine in options available.
Post-Hike Suitability: Exactly what you need after burning calories on Cobble Mountain. It's casual, fast, and satisfying. Grab a table or order carryout, and make sure to try the buffalo cauliflower as a must-order appetizer.
Swyft
Address: 3 Maple Street, Kent, CT
Price Range: Moderate to Upscale ($$ to $$$; small plates roughly $15 to $30, entrees $25 to $45)
Current Operating Days: Open Thursday through Sunday for lunch, brunch, and dinner service, closing out dinner by 9 PM (closed Monday through Wednesday).
Reservations: Highly recommended, especially on weekend evenings when the village gets busy.
Post-Hike Suitability: Offers a great atmosphere for grabbing a high quality, wood-fired tavern meal in the heart of town. You will want to brush off the dust before sitting down, it's an unbeatable spot to unwind with great food after a long day.
Local Shops, Galleries & Stops in Kent
Kent is highly walkable, making it incredibly easy to add on a few stops between your hikes and your meals.
Kent Barns: A gorgeous complex of restored historic barns right off Main Street that now house art galleries, boutique shops, and eateries. It is an architectural dream to walk through.
House of Books: I am a sucker for an independent bookstore. This is right on Main Street with a decent selection.
Tarot in Thyme: Take some time to wander throughout the shop. It's packed with boutique clothing, jewelry, crystals, books, and more.
Sculpturedale: A totally unique outdoor experience wandering through incredible metal animal sculptures set across beautiful grounds.
Quality Thrift Shop: Run by the local church, this is a fantastic little spot to hunt for hidden gems and vintage finds.
Westerlind: A little expensive, but outdoor gear is worth it!
Where to Stay Near Kent, CT
I usually visit Kent as a day trip, but if you want to turn this into a full weekend, these are the most popular lodging and camping options hikers choose.
The Kent Collection: Beautiful, boutique accommodations right in the walkable village.
Cooper Creek Bed and Breakfast: A classic, cozy New England B&B experience.
Club Getaway: A camp-style resort with cabins and activities.
Mt. Algo Shelter & Lean-to: Primitive overnight stops right on the Appalachian Trail for backpackers.
Schaghticoke Mt. Campsite: Another rustic AT camping option for through-hikers.
Macedonia Brook State Park Campground: Great car-camping right near the trailheads.
Lake Waramaug State Park Campground: Scenic, lakeside camping just a short drive from Kent.
Best Time of Year to Visit Kent
Kent changes dramatically with the seasons. Here is what to expect so you can plan appropriately.
Season | What to Expect |
Spring | The waterfalls are flowing in full force! It is a fun, adventurous time to visit during the spring rains, but stay on the trail and away from the fast-moving river. |
Summer | Perfect for long days on the trails and cooling off. Add a quick trip to nearby Lake Waramaug for swimming. |
Fall | Peak New England foliage. Expect heavy crowds at Kent Falls and busy trails. Conditions can get muddy. |
Winter | The trails empty out, offering total peace and quiet. Mandatory: Pack micro-spikes for all trails. |
Can You Do Kent, CT as a Day Trip?
Yes, absolutely. Kent is practically designed for day trippers. It is an easy drive-in, drive-out town. You can stack one or two short hikes in the morning, grab a great lunch, wander the shops, and be back on the highway before dinner.
Frequently Asked Questions
Are dogs allowed at Kent Falls State Park? Yes, dogs are allowed at Kent Falls State Park, but they must be kept on a leash at all times. Be very careful on the stone stairs with your pup, as they can get slippery!
Is downtown Kent walkable? Yes! The main village of Kent (along Route 7/Main Street) is very pedestrian-friendly. You can easily park your car once and walk to the local coffee shops, Kent Barns, and art galleries.
Ready to hit the trails? Make sure you grab my free packing list below so you don't forget any essentials before heading into the Litchfield hills!
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