20 Activities To Do In Connecticut This Fall

20 Activities To Do in Connecticut This Fall

20 Activities To Do In Connecticut This Fall

In 2020, my family closed on our beach house in Connecticut during the end of August, so naturally I tried to drag the summer out for as long as possible. It was mid-September, and I was still laying out on the beach trying to keep my tan. During the evenings, Billy and I would go for runs around the neighborhood, which was something I looked forward to. We left Connecticut for a week in mid-October to look for an apartment in New York City. Once we returned, the weather had shifted. I traded in my shorts and tank tops for a pair of leggings and my North Face jacket. As we stepped outside to go on our daily run, the aroma of a wood-burning stove filled the crisp fall air. At that point, I was fully ready to embrace autumn, which was the first time since I had moved to Los Angeles almost 10 years earlier. I looked forward to watching the leaves turn shades of red, orange, and yellow and made a list of fall-related activities that I wanted to enjoy. Billy and I had no idea when an apartment would be available, so we tried to cram in as much as possible. 

A year later, and we’re living in and enjoying life in NYC but I plan on taking a trip or two back to Connecticut. I can’t wait to partake in the quintessential New England autumn activities, like strolling the quaint towns of Madison and Mystic, and picking pumpkins at Strawberry Hollow Farms in Guilford. I’m also looking forward to the scenic train ride from Penn Station to Old Saybrook since the majority of it goes through the woods and I’ll be able to see the stunning fall foliage. Below are 20 autumn and Halloween related activities that I’d like to do while I’m in Connecticut. 

1. Take in the colorful autumn leaves by hiking in Devil’s Hopyard State Park. Some have claimed that it’s haunted making it ideal to visit right now, and there’s a picturesque bridge I’d like to see in person. Here’s an interactive fall foliage guide for Connecticut which tells you the stages of the leaves based on the location. 

2. Spend the day shopping in Madison where there are so many independent boutiques, gift shops, and cafes like Walker Loden Ltd., J. Horton, Robertson Madison, Creations Gift Shop, Slate, and RJ Cafe + Bistro. This charming town reminds me of Stars Hollow, the fictional village in Gilmore Girls.

3. Have lunch at the Griswold Inn and then stroll the quaint streets of Essex. Last year, Billy and I did this, and it was an ideal autumn day. The inn is one of the oldest in the United States, dating back to the 1800s, so there’s a lot of history there. After lunch, we stopped in the old-fashioned gift shops and stores, and then walked down to the water.

4. Stop by the Let’s Scare Jessica To Death house. You can’t go inside the vacant house, but you can take photos of the creepy exterior from the street. 

5. Go on a haunted hayride. I haven’t been on one since I was a teenager and accidentally kicked a worker off when I got scared.

6. Explore The Book Barn, which is one of the most unique book stores I’ve come across. There are three locations (The Main Barn, has the largest selection of genres spread out in several buildings. There are also cats, goats, and gardens. The Downtown Store is in the heart of Niantic Village. Then, there’s Chapter Three, which is located 300 feet from the Main Barn. All three shops are within a mile of each other and some have claimed one of the buildings at The Main Barn is haunted.) 

7. Have dinner at the colonial Captain Daniel Packer Inne which was built in the 1700s. Guests and employees have reported seeing the ghost of Captain Parker, and his great-niece Ida.  

8. Find the perfect pumpkins to carve and pick seasonal produce at Strawberry Hollow Farms. After visiting last year, it immediately put me into the fall spirit. There are stunning displays of picture-worthy photo ops. 

9. Tour Kent and New Preston, the towns where Friday The 13th Part II was filmed.

10. Make a fall favorite like vegan chilli, tomato soup, apple pie, or caramel apples.

11. Have afternoon tea at the Old Lyme Inn. This time of the year, they have seasonal favorites like pumpkin spice and cinnamon sugar scones with cider butter, mini pumpkin pies, and tea sandwiches.   

12. Visit the Trail of Terror, a haunted attraction that takes place in the woods. 

13. Go thrift shopping and hunt for antiques. Connecticut is home to many unique second-hand stores. A few I want to check out are the Clinton Antique Center, Tova’s Vintage, and The Essex Saybrook Antiques Village.

14. Walk around Mystic Village and stop in Deviant Donuts. This was on my summer bucket list, but when I visited, they were sold out. Now, I’m excited to try their fall donut flavors like chai, pumpkin spice, and cinnamon sprinkles. (Their menu changes weekly.) 

15. Make stovetop pot-pourri (I mix orange, apple, and lemon slices with cinnamon sticks and cloves), and watch a Halloween film as it simmers. Here’s my list of favorites.

16. Have a picnic on the beach and prepare a charcuterie board with a variety of cheeses, crackers, nuts, and jams. Also, make spiked hot apple cider, and bring plenty of thick blankets

17. Purchase apple cider, apple pie, cider donuts, and other fall treats at Bishop’s Orchards Farm Market & Winery. Last October, Billy and I visited for the first time and spent hours shopping for seasonal and organic items.

18. Try a cozy cocktail from the Marina Bar at Saybrook Point. I’d love to try the Caramel Apple Martini, the Apple Cider-Car, or the Woodford in Manhattan.

19. See the “possessed” Snedeker House in person which inspired the book In a Dark Place: The Story of a True Haunting and movie, The Haunting in Connecticut. It’s a private residence, so it can only be viewed from the street.

20. Go on a ghost tour in New Haven and hear about it’s haunted history!

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