One of the many things I love about living in New England is how easy it is to explore the region. There are so many incredible places for a day trip or overnight getaway, and Litchfield County is always one of my top recommendations if you’re looking for a relaxing weekend in Connecticut.

Between the quaint historic towns, farm stands, independent shops, great restaurants, vineyards and some of the prettiest countryside in the state, there’s so much to do without ever feeling like you have to rush from place to place. And if you’re a Gilmore Girls fan like me, this part of Connecticut definitely gives off allll the Stars Hollow vibes.

I recently spent a couple of days here, staying in Litchfield and making stops around Bantam, New Preston, Washington and New Milford. Here’s everything we did and how I’d plan the trip.

Where to Stay: The Red House 1735

We stayed at The Red House 1735, a historic home right on Bantam Road in Litchfield. Built in 1735, it’s one of the oldest houses in town, and you can actually book the entire house for an overnight stay.

One of my favorite things about staying here was that it still really feels like an old New England home. There are plenty of modern updates, especially in the kitchen and bathrooms, but it hasn’t lost the little quirks and details that give a historic house its character.

The grounds and backyard are also beautiful, with plenty of space to relax, have coffee outside in the morning or do dinner at the house with friends.

The house sleeps six, so it’s a great option for a weekend with friends or family. The location was also a huge plus. You’re right on Bantam Road, close to both Bantam and downtown Litchfield, with White Memorial directly across the street.

Morning Coffee + One of My Favorite Bakeries

The next morning, we started with coffee at Krafted Brew Lab, which is literally about a minute down the road from the house. It’s a really quaint coffee shop that is my favorite in the area. I always get an iced maple latte!

From there, we went to Bantam Bread Company, a longtime favorite of mine and a place I pretty much always recommend when someone is visiting Litchfield County.

Everything is made in-house, and I especially love their focaccia and Dirt Bombs, which are little spiced cakes covered in cinnamon sugar. They’re buttery, delicious and definitely worth trying.

I recommend getting here earlier in the day since they can sell out!

Explore Downtown Litchfield

After breakfast, we drove into downtown Litchfield to walk around the town green and browse some of the shops.

A few of my favorites are Milton Market, CP Farmhouse and The Homestead Collective.

Litchfield is one of those quintessential Connecticut towns that’s worth visiting even if you don’t have much of an agenda. Take some time to walk around the green, pop into a few local shops and explore before heading to your next stop.

Lunch + Shopping in New Preston

Next, we drove over to New Preston, one of my favorite tiny villages in Litchfield County.

We had lunch at The Smithy Market, a café and marketplace with prepared foods, local produce, pantry items and other finds. It’s a great casual lunch stop before spending some time exploring the shops nearby.

And when I say New Preston is small, I mean it. The main shopping area is basically one little stretch of road, but there are some really good stores packed into it.

J. Seitz & Co. is one of my favorites, with a mix of home decor, furniture, clothing and gifts. Make sure you walk all the way through the shop and head out to the back patio, too. There’s a beautiful waterfall tucked right behind the building that feels like a hidden little spot in town.

Wine Tasting at Spring Hill Vineyards

From New Preston, we headed to Spring Hill Vineyards, which is just a short drive down the road.

This is such a fun vineyard to visit during the summer because it’s more than just a place to have a glass of wine. The property itself is beautiful, with sculptures scattered throughout the lawn and lots of space to sit outside.

We did a wine tasting and spent some time enjoying the property before continuing on with our afternoon.

Stop at Hickory Stick Bookshop + Ice Cream at Arethusa

On our way back to the house, we stopped in Washington Depot at Hickory Stick Bookshop.

This is one of my favorite independent bookstores in this part of Connecticut and absolutely worth popping into if you’re nearby. It has that cozy, small-town bookstore feel and a really good selection of books and gifts. Washington Depot itself is also worth a quick wander if you have extra time.

Before heading back to the house, we grabbed ice cream at Arethusa which is one of the best ice cream shops in Connecticut.

Dinner at Community Table

After relaxing at The Red House for a bit, we headed to Community Table for dinner.

I’ve been here several times, and it might be my favorite restaurant in Connecticut. The space is beautiful without feeling overly formal, the service is always great, and the food is consistently incredible. One of the things I love most is that the menu is constantly evolving with the seasons, so dinner here can feel completely different depending on when you visit.

If you’re planning a weekend in Litchfield County, I would absolutely make a reservation here ahead of time.

Morning Walk at White Memorial

The next morning, we headed across the street to White Memorial Conservation Center for a walk.

White Memorial has miles of trails, but if you’re looking for something easy, the boardwalk is one of my favorites. It takes you through the wetlands and has beautiful views without requiring a serious hike. This would be a great one with kids too!

Staying at The Red House made this especially convenient since White Memorial is directly across Bantam Road. We could get outside for a morning walk and then head back to the house before checking out.

Farm Stops on the Way Home

No Litchfield County road trip is complete without at least one farm stop, so on our way back toward Stamford we stopped at Thorncrest Farm and Ox Hollow Farm Stand.

Thorncrest is home to Milk House Chocolates, where chocolates are made using milk from the farm’s cows. It’s such a unique Connecticut spot and an easy addition to a drive through this part of the state.

We also stopped at Ox Hollow Farm Stand before continuing south.

One Last Stop in New Milford

Instead of heading straight home, we made one final stop in downtown New Milford.

If you’ve never been, New Milford has one of those classic New England downtowns with a huge town green, gazebo, historic buildings and locally owned shops. It definitely gives me that Gilmore Girls Stars Hollow feeling.

Take some time to walk around the green and browse the shops. I also love River & Rail Café if you want coffee or something to eat before getting back on the road.

A Summer Weekend in Litchfield County

This was such an easy two-night Connecticut getaway and a good reminder that you really don’t have to travel far to make a weekend feel like a vacation.

You could follow this itinerary pretty closely, but I also think Litchfield County is best when you leave yourself a little extra time to pull over at a farm stand, wander into a shop you didn’t plan on visiting or just take the scenic route.

Save this itinerary for your next Litchfield County getaway and check out my reel HERE.