9 Adventurous Day Trips in Connecticut; Hikes, Food, & Fun!
There are so many opportunities for fun and adventures in Connecticut! And there are so many charming CT towns worth visiting and making a special trip to!
🌟In this post, I’ve included 9 very special day trip destinations in CT. And I don’t just give you one or two things to do for visiting each town…
Instead, I have a whole post and itinerary dedicated and linked for each CT day trip so you don’t have to worry about doing the research and planning. You will be supplied with all the best things to do in each destination!
With a huge love of hiking, adventure, small-town charm, and the best food and living in Connecticut almost all my life – I’ve consistently sought out the best places to visit here.
If I have a day off from work I’m brainstorming what new town to drive to and discover and also lining up trips for the weekend. 🚗🚗
When deciding what town is worth an hour or more trip in the car each way, I always look to see if it has the following winning combo: scenic outdoor places and hikes, charming downtowns to stroll, and excellent cafes and restaurants! ☕️🥾🥐
You can be sure that if you learn about it here in this post – you will have fun and however long you have to drive to visit these CT spots will be worth it!
Whether you’re coming from New York, Massachusetts, or someplace within our beautiful state – you will find your next CT adventure here!
So let’s get to it, friends! ⬇️🚗
The BEST Day Trips in Connecticut (and Activities for Each!)
1. Granby, CT 🚗
➡️ Full day trip itinerary for Granby 🔗
Granby is located on the northern edge of Hartford County (bordering MA!) and gives you every bit of that quaint rural feel. The destinations in Granby that I’d encourage you to visit are spread out.
This is a CT town to visit if you want that windows down, free country feel – driving from spot to spot that I recommend below. Granby has TONS of hikes and walks to choose from given its home to the vast McLean Game Refuge along with Holcomb Farm Land Trust Trails.
🌟 Must-do in Granby: Julien’s Farm Store (bakery!) ➡️ Holcomb Farm Trails ➡️ Old Mill Pond Village
A day trip to CT list would not be complete with perhaps the most famous Connecticut town. Although I’ve never seen the show, Gilmore Girls is apparently a big deal and Washington Depot inspired the charming, idyllic town you see in the show.
Washington Depot’s downtown area is small but very picturesque. It has a few shops and multiple cafes in one area, you can park and walk to all of them.
And then a short drive away from the downtown is a vineyard, sprawling farm where you can pick apples or get pumpkins in the fall, and very close to downtown is the must-visit Steep Rock Preserve (where you can walk through the old railroad tunnel from 1871!) or the 700-acre Hidden Valley Preserve with the hanging bridge over the Shepaug River.
🌟 Must-do in Washington Depot: The Pantry 🥐, Hidden Valley Preserve 🥾🌲, Spring Hill Vineyards
Charm, charm, and more charm! Salisbury is what you picture a classic New England town to be – a Main Street you can stroll with shops and restaurants on either side, a white-steepled church on one end, and a large historic inn on the other.
Here you can park and walk around Main Street to eat, shop, visit a vibrant Civil War Memorial, and even access and start walking on the Railroad Ramble – a rail trail that connects Salisbury to Lakeville.
Located in northwest CT, Salisbury is surrounded but some of the best hiking in the state since the Appalachian Trail runs right through it! There are also easier trail options here like the Salisbury Land Trust. All are linked below in my full post all about Salisbury.
🌟 Must-do in Salisbury: Sweet William’s Bakery 🥐, shop & stroll Main Street 🛍️, Rand’s View 🥾, White Hart Inn
I know, a lot of these towns are in the northwest corner of our state but once you visit one of them – you’ll see why I keep coming back to this part of CT!
Sharon is the definition of timeless New England rural beauty! The rolling hills surrounding the classic town green with the library on one side, historic old homes, a cafe and, a couple of stores. You’ll feel transported to a picture-perfect town!
This is the perfect CT destination for quiet, beauty, rural scenes worth pulling over for on the way, and tons of land trusts in Sharon to explore! These are easy walks for most abilities. You can get to jaw-dropping views with very little effort!
🌟 Must-visit in Sharon: J.P. Gifford Cafe 🥐, Sharon Land Trust 🌲🥾, Lime Rock Park Racetrack
Yay, a destination in Fairfield County! I do want to explore this part of CT more but it’s just hard to avoid the pull of the northwestern corner. But if you’re coming from NYC or a spot in NJ, Newtown will be the closest for you and – it’s very much worth a visit!
You might think of towns in Fairfield County as busy or bustling but surprisingly, Newtown is the 5th largest town, area-wise, in our state. And it’s not as built up as other nearby towns so you get that relaxing country vibe and scenic drive as you head in.
There are incredible destination-worthy restaurants in Newtown along with a chocolate shop with truffles & a chocolate-covered Oreo that I still think about today.
And you’ll be able to work all that off at your choice of a nearby sanctuary, waterfall walk, or loop along the Housatonic River which runs through Newtown. This town has it all and I encourage you to visit my full Newtown post and plan your trip!
🌟 Must-visit in Newtown: Castle Hill Chocolate 🍫, Rockhouse Hill Sanctuary 🌲🥾, Foundry Kitchen & Tavern
I lived in Litchfield, minutes from downtown Main Street, for years, and it was a dream. Hence why I frequently go back to visit and wanted to write all about it for you here.
Out of all the towns listed above, Litchfield has perhaps the best Main Street. The Litchfield Green on one side (where concerts and craft fairs are held) with shops and restaurants lining the other.
My favorite gift shops are located here PLUS there are 4 different cafes within half a mile competing for your attention. Not to mention a couple of the best restaurants in our state; Arethusa and Materia Ristorante.
One of my favorite things to do in Litchfield is park somewhere near or on Main Street (usually never a problem to get a good spot) and walk up and down North Street and South Street and admire the super old and huge homes.
And then, if you want more of a woods walk take your pick from the 4,000-acre must-visit White Memorial Conservation Center and several Litchfield Land Trusts. I know you will love it here!
🌟 Must-visit in Lichfield: Topsmead State Forest 🌳, stroll & shop Main Street & North Street 🛍️, White Memorial Conservation Center 🥾🦫
7. Cornwall, CT 🚗
➡️ Full day trip itinerary for Cornwall 🔗
The longest covered bridge in Connecticut, bakeries nestled among Mohawk State Forest and the hills of the Appalachian Trail, antiques, and some of the most scenic roads and hikes in CT.
You will love a visit here! This is more of a drive around and make stops kind of town compared to Kent (listed below) where you can park and walk up and down Main Street.
But that’s what makes Cornwall a beautiful place in CT to visit for a wide-open, country feel, with some of the best hiking in our state! The town probably still looks a lot like it did 200 years ago which I love.
🌟Must-do in Cornwall: Housatonic River Walk (flat) 🥾, Blue Gate Bakery 🥐 , Ivy’s Collective 🛍️, West Cornwall Covered Bridge 🌁❤️
8. Kent, CT 🚗
➡️ Full day trip itinerary for Kent 🔗
Here we have another town in northwestern CT but this is a REALLY good one. Kent is another CT town with a charming Main Street for you to stroll and LOTS OF SHOPS to pop into!
Kent feels like a true mountain town with the Appalachian Trail mountains as its backdrop. Feel your adventurous spirit come alive here.
You’ll want to park and walk on both sides of Main Street, hit the chocolate shop and bakery (45 on Main), and then take your pick of the vast array of hiking choices from Kent Land Trusts to a spot along the Appalachian Trail. (Find it all linked in my Kent post below!)
Also, I would STRONGLY suggest eating at Kingsley Tavern (right on Main St!). They have a seasonal menu focused on local ingredients when possible, were featured in the NY Times, and, a place whose dishes I dream about. I’ve eaten here twice and plan to keep coming back!
🌟 Must-visit in Kent: 45 on Main 🥐☕️, Kingsley Tavern 🍔, Kent Land Trust Trails 🥾, Caleb’s Peak on the Appalachian Trail 🥾
9. Falls Village (town of Canaan), CT 🚗
Falls Village is where you should take a day trip in CT if you want rural beauty that makes you feel like you’re in another state! Vermont, maybe?
Visit here if you want breakfast or lunch at the amazing Mountainside Cafe, followed by a hike on the Appalachian Trail, and a visit to one of the largest waterfalls in CT, Great Falls. This is a more rural CT day trip without a Main Street with shops, etc.
I like the way CTVisit describes it; “One visit to Falls Village and you’ll feel transported back in time to the mid-1800s. The churches, railroad depot, Inn, bank, streets, and houses maintain their 19th-century integrity, offering an accurate picture of the community’s organization a century and a half ago.”
🌟 Must-visit in Falls Village: Mountainside Cafe 🥐, Great Falls 💦, Appalachian Trail hike 🥾
So that’s it, friends!
Which CT day trip spot are you going to next?! I’d love to hear what you think if you go to any of these places. Also, please leave a comment or any questions below! 💌
⬇️ For more CT travel ideas check out the following posts:
