When you think of Litchfield County in Connecticut, picture scenic hikes and trail walks, farm-to-table restaurants, charming downtowns, and historic sites (including the site of the earliest law school).

This part of Connecticut sits along the Western side of the state close to the New York border. There are also several towns to explore in this scenic rural area which makes it a perfect day trip destination or overnight stay.

And while I visited in winter, these destinations can be enjoyed year-round.

Your 12-Step Guide for a Fun Visit to Litchfield

1 - But first, coffee… (Litchfield, CT)

Start your trip with a delicious cup of coffee from one of the many cafes and coffee shops.
Two of my favorite spots I visited are:

Krafted Brew Lab - Strong and flavorful coffee! They also have coffee beverages. I had a maple latte with oatmilk and it was so good!
Toast & Co - Delicious coffee and coffee beverages alongside a full list of breakfast and lunch sandwiches.

2 - Take a Walk (Litchfield, CT)

There are so many great trails in the area. If you love a boardwalk trail, head to White Memorial Conservation Center and take the Little Pond Boardwalk Loop trail. You’ll follow an elevated boardwalk trail for about 1.2 miles through the wetlands around Little Pond. The views are great and it’s such a peaceful walk. And the best part is you really can’t get lost since the trail follows a loop around the pond.

3 - Enjoy the Best Sandwiches (New Preston, CT)

If you like an artisan sandwich as much as I do, then get ready because you are in for a real treat. The Smithy Cafe in nearby New Preston has some of the best sandwiches I have every had. Many of the ingredients are locally sourced and always super fresh. I always order the “The Waramaug” which has turkey, havarti cheese, sliced cucumber, sprouts, basil, sunflower seeds and mayo on multigrain bread - perfection!

4 - Walk the Henry David Thoreau Footbridge (Washington Depot, CT)

This 134-foot-long footbridge stretches across the Shepaug River in Washington Depot’s Hidden Valley Preserve. As you make your way across the bridge you will find a quote from Thoreau greeting you -“The universe is wider than our views of it.” There are some beautiful views from the bridge and it’s really fun to cross, as this suspension bridge definitely has some bounce to it. From the bridge you have the option to hike a variety of trails within the preserve. Check out the Hidden Valley Preserve trail map here.

5 - Explore a Town that Inspired the Gilmore Girls (Washington Depot, CT)

I can’t say that I have ever watched popular Gilmore Girls TV show but after visiting the town of Washington Depot I definitely need to! Washington Depot has such a quintessential town center and it’s known for one of the cutest bookstores. The Hickory Stick Bookshop is packed with books alongside games and other cute items. And if you are a mystery lover like I am, then this spot is for you because they have a huge mystery book section.

The creator of Gilmore Girls spent time in Washington Depot and drew inspiration for the show’s fictitious town setting “Stars Hollow” from the look and feel of Washington Depot.

6 - See Connecticut’s Tallest Waterfall (Kent, CT)

Make your way to Kent, CT for a visit to one of the many state parks in Connecticut. Kent Falls State Park is a beautiful spot to visit year round and is home to the tallest waterfall in Connecticut, with an impressive 250-foot drop and several cascades . The base of the waterfall can be accessed via a paved path from the parking area and you even get to walk through a covered bridge along the way!

From the base of the waterfall you can take the Kent Falls Steps Trail, which will take you alongside the waterfall to view the multiple cascades from viewing platforms along the trail.

The trail is fairly steep but is well groomed and maintained, with most of it consisting of a series of steps. The viewing platforms allow for spots to take a break along the way to the top. While the trail is steep, it is short and only about 0.25 miles to the top. Once you reach the top of the trail you can go back the way you came or opt to take the red-blazed trail back to the parking area.

In the warmer months you will likely find visitors enjoying a picnic at the many tables in the park and in the winter you may find visitors sledding here.

The park is open from 8 am - sunset and a bonus of visiting in winter is that there is no entrance free (entrance to the park can be $10-15 for out of state vehicles depending on when you visit).

7 - Experience Connecticut’s Wine Trail (Warren, CT)

There are several wineries in the area to explore and many more along the full CT Wine Trail. I recommend making a stop by Hopkins Vineyard which is open year round and has great views of Lake Waramaug. I love that they offer wine flights so you can try a few of their wines - favorite was the apple wine. Take your flight up to the second floor of the winery for a seat with views out to the lake.

8 - Try an Old Fashioned Ice Cream (Litchfield, CT)

I am a huge ice cream fan and will easily travel multiple hours for a good scoop. I can say that Arethusa Farm Dairy delivers some of the best ice cream I have ever had. If you are an ice cream fan, you need to stop here! I love the unique flavors they offer like the Pumpkin Ginger Molasses Cookie (a unique and seasonal spin on classic cookie dough).

9 - Visit the First Law School (Litchfield, CT)

Did you know that Litchfield is home to the site of the earliest law school in the United States? The Tapping Reeve House and Law School is a registered national historic landmark. While the inside is closed in winter and reopens to visitors in January, you can still explore the outside of the building and take a peek in the window. If you enjoy New England history, I recommend making a stop here. This location is also close to the center of town and makes a great stop on a walk around Litchfield town center.

10 - Shop Local in Litchfield’s Town Center (Litchfield, CT)

There are so many small local shops and restaurants in the center of Litchfield. One of my favorites is Milton Market which offers lots of locally sourced and handmade items. The selection of items rotates frequently, so there is always something new to see!

11 - Step into the Cutest Chocolate Shop (Goshen, CT)

Thorncrest Farm is a must-visit spot if you’re visiting Litchfield County in Connecticut and was one of my absolute favorite stops on my trip. Located in Goshen, CT, less than 10 minutes from Litchfield town center, you will find delicious chocolates and a working farm.

If you’re looking to shop local, this place is it! Their chocolates are beautifully packaged, and there are so many to choose from. You can even visit the barn and meet their cows. All chocolate production is done on-site, and the farm is exceptionally clean and organized. Depending on when you visit, you may even be able to see baby cows.

The store is open daily from 10–5 (be sure to check their site for any holiday closings before you head out).

12 - Dine at a Farm to Table Restaurant (New Preston, CT)

Litchfield County is known for their delicious dining options and Community Table did not disappoint. The menu rotates weekly to ensure the freshest ingredients and seasonal offerings. The cocktail menu is unique and each is crafted with care. I tried the “Winter Warmer” made with gin, fresh mint, and rosemary. And if you’re looking for mocktails, then Community Table has you covered with their curated list of zero-proof cocktails.

I recommend making a reservation in advance as tables are limited and this spot is popular.

Where to Stay

I stayed at the The Litchfield Inn in Litchfield, Connecticut. This luxury boutique inn is perfectly located just minutes from the Litchfield town center where you will find lots of shops and restaurants and it is also close to all of the above destinations. See my blog post “A Luxurious Getaway to Litchfield, Connecticut” for all the details.

A Winter Trip to Litchfield County, Connecticut