9 Things to Do in Kent, CT in the Fall

Show your true red, orange, yellow, and green colors this autumn. Here are 9 things to do in Kent, CT in the fall including hikes, art galleries, book sales, car raffles, pumpkin runs, and more.

Fall is my favorite season of all. People think I’m funny when I list out my reason why, I sounds like I’m narrating a movie. My love for autumn has nothing to do with Halloween, in fact I’m not a big fan of the holiday. What I love are the stunning colors (some may say October is my favorite color), the crisp air that’s not too hot and not too cold, the craving for apples, pies, pumpkins, and hearty food, the fact that we can finally pull out our boots, sip hot chocolate, and wander the city and back country under layers of sweaters, coats, and scarves.

Unfortunately, fall is also the most fleeting of all seasons and you have a short window of time to enjoy it. That’s why every year I try and do a new fall weekend getaway from NYC to enjoy the season and bask in the fall foliage. This year I moved away from the more frequented state of New York, and decided to turn to my own home state of Connecticut. Here’s your guide the many things to do in Kent, CT.

1. Drive up famous Route 7

Pat and I decided to take the longer route from Greenwich, CT to Kent, CT. We drove down the famous Route 7 from Norwalk up to Litchfield. I think Patrick wanted to kick me out of the car on our way up. I couldn’t stop gawking at every tree like I had never left New York City. Which is hysterical, because I spent the majority of my life living in the suburbs and never batted an eye. I guess that’s what the city does to you. On top of that, there were spells of incredible carpeted autumn colors, rolling hills, and lush forests, and spells of naked, empty trees. I kept saying, “The foliage is still here! No, nope, I made a mistake, we’re too late, the foliage is gone…no, I’m wrong look at these colors! No, no, they’re gone again.” And the cycle repeated itself. Needless to say, the colors were still there when we arrived.

2. Hidden Scenic Routes: Treasure Hill Road

To be honest, I didn’t find Route 7 to be THAT amazing. It was worth the drive, but nothing too crazy. My favorite area actually was Treasure Hill Road in my video above. It is a secret area legitimately built for scenic fall foliage drives in the heart of the suburbs. In fact, signs constantly appear left and right that say “CAUTION: Scenic Route.” I couldn’t help but laugh when I saw those signs, who needs a sign that says caution scenic route?! But Patrick said they were meant for people like me who constantly get distracted by beautiful scenery. He’s right!

3. 1872 Old Train Depot

When we finally pulled up to Kent, CT, we found a parking spot in front of the train station at the end of the short town strip. The main town is located on one small and short road called, of course, N Main Street. It’s hard to miss the old train depot from here. It’s a beautiful 1872 depot, whose outside remains unchanged. It looks like a big red barn with light blue doors. We hear live music playing from a restaurant across the tracks, where people are drinking and sitting outside. We continue down Main Street.

4. Annual Book Sale & Car Raffle

The annual book sale was happening on Library Street. It apparently goes on from Memorial Day to mid-October. It is the Kent Memorial Library’s biggest fundraiser, and all proceeds benefit the library’s operating budget. Every year, alongside the book sale, a $20 buy in car raffle takes place as well. This year, the winner would get a 2000 Porsche Boxster Roadster. I tried to convince Pat to buy a ticket, but we needed to be present the day after when they announced the winner at the annual Pumpkin Run and we weren’t planning on staying overnight.

5. Arts. Everywhere.

If there is one thing Kent, CT is known for, even more so than foliage, it’s its strong presence in the arts. That’s why visiting one of the many art galleries is on the top list of things to do in Kent, CT. As you stroll around town you will come across a number of art galleries throughout town, but also encounter Joy Brown and Peter Busby’s famous metal sculptures placed throughout town along the way. My favorite Busby art sighting was the whale tails that shot up from the ground next to Library Street.

6. Kent, CT Restaurants and Food

The truth is, Pat and I came to Kent with one main objective, to hike through CT’s incredible mountains and truly lose ourselves in the foliage. The many other things to do in Kent, CT were just an added bonus to our stop. Before embarking on our 7-mile hike in Macedonia Brook State Park, right next to Kent, we needed to load up on carbs. Had we had more time, I would’ve sat outside and enjoyed a wonderful sit down meal in one of the many beautiful outdoor cafes and restaurants. Because we were short on time, we stopped by one of the best sandwich shops in town, J.P. Gifford, for a quick bite. There sandwich options are unbelievable and their hot chocolate is apparently very good as well.

7. Kent Barns

Kent Barns is located right behind House of Books. It’s a series of six restored and re-built historic barns that now host a variety of shops, galleries, restaurants, and other businesses. From cheese markets to woodworking, fine art, books, Swyft for wood-fire pizza, RT Facts for home adornment, and more. In addition to Kent Barns, you’ve also got a ton of craft stores, vintage and antique stores, and thrift shops along Main Street to peruse. You’d be surprised to find some exotic and unique finds you wouldn’t expect to find in the middle of CT.

8. St. Andrew’s Parish Hall

Kent Affordable Housing throws regular fundraising events for various housing projects in the area such as renovating and constructing five rental apartments in an antique farmhouse close to the center of Kent. During our fall weekend getaway from NYC, one of these events was taking place called “Home Made for Kent Homes” at St. Andrew’s Parish Hall. Until 3PM (and if there is anything still available by then!) you can buy baked delicacies from local kitchens and bakers. Patrick and I were tempted, but we ended up deciding that a pie sitting in our car while we hiked for 5 hours wasn’t the best idea.

9. Hike Macedonia Brook State Park

After tearing me away from the charming town of Kent, CT, Pat and I finally made it to Macedonia Brook State Park. Afterall, no fall weekend getaway is complete without a foliage hike. We decided to take on the 6.8 mile Brook Loop blue trail that completes a perfect circle around the park and includes stunning views from Cobble Mountain. It’s the toughest of the trails, but the most rewarding and secluded of them all. There are also easier trails for those looking for a casual short stroll through the park. More on my hike here.

Like Cinderella, fall is fleeting. When the clock strikes midnight, fall ends in a snap and Christmas is in full swing. So when those weekends from October 16 – 30 roll around, don’t miss out on the occasion to surround yourself in that peak foliage. Show your true red, orange, yellow, and green colors, and head to Kent, CT for fall weekend getaway from NYC. And after a beautiful afternoon exploring Kent, prepare yourselves because–Winter is coming. And this year is said to be one of the coldest we’ve had in a while…

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