The Litchfield Hills in Connecticut is a great destination in October. We love to enjoy a fall drive or weekend away in Litchfield County once the leaves change. It’s such a beautiful region in Connecticut full of farms, gorgeous state parks, award-winning farm-to-table restaurants, and charming towns with boutique shops. It’s full of New England charm, and home to two of the three remaining covered bridges in the state. We just returned from our fall weekend away there, and here are some of our favorite places in the Litchfield Hills.
stay
Two favorite places to stay when we are in the Litchfield Hills are The Abner Hotel and The Mayflower Inn & Spa.
The Abner is a boutique hotel in Litchfield right in the center of town across from the town green. The hotel is the historic courthouse that has been renovated into 20 rooms and suites including an on-site restaurant and roof-top bar. They offer a nice breakfast for guests during their stay, and the location is wonderful.
The Mayflower Inn & Spa is a luxury hotel in Washington with a wonderful restaurant, bar, and full-service spa. The interiors are designed by interior designer, Celerie Kemble, and the grounds are just beautiful. I love the well-appointed rooms, and cozy common spaces. It’s a lovely place for a romantic getaway, and a wonderful place to relax and have a spa day with your girlfriends.
Another one on my radar, but I haven’t stayed at yet, is Winivan in Morris. This Relais & Chateaux property offers luxury cottages and a famed restaurant. We are kicking around booking this one for our next anniversary. It looks amazing!
dine
Litchfield County is known for its farm-to-table restaurants, and many are award-winning. We have a lot of personal favorites we have enjoyed every year. I would suggest securing a reservation in advance, especially during peak foliage season.
Arethusa al tavolo in Bantam is a lovely dinner spot with a cozy, intimate atmosphere. This famous Arethusa Dairy Farm restaurant offers a seasonal dinner menu highlighting its award-winning cheeses and ice cream too.
Ore Hill is another favrorite of ours in Kent. It’s one of the top restaurants in the area featuring a tasting menu with everything sourced from local farms. It’s a lovely setting for a cozy candlelit dinner.
The Garden Room and Tap Room at The Mayflower Inn in Washington is another favorite spot to enjoy a meal. The Garden Room is lovely for a farm-to-table brunch or lunch. Everything is sourced locally and changes with the season. The tap room is so cozy for dinner and we love to head out to the fire pits outside with an after dinner cocktail. You can’t go wrong dining at either restaurant.
The Courtroom at The Abner Hotel in Litchfield has a unique farm fresh menu. Some dishes have a little global influence. We love their seasonal drink menu and fresh take on some classic dishes. They offer brunch on the weekends.
G.W. Tavern in Washington Depot is a cozy atmosphere for lunch or a casual dinner. If you are in the mood for pub food done right, this is the place to enjoy a fireside meal. If you go in the fall, be sure to get their mulled cider.
shopping
The best way to shop around the Litchfield Hills is to take a leisurely drive and do it town by town. New Preston, Litchfield, and Washington are my personal favorite towns to stop in to shop, so I’m going to stick to the ones we frequent the most. I’m not including any chain stores on this list, because we have an abundance of those where we live in Connecticut.
In Litchfield: Hope & Honey Gift and Bookshop, I Ching Antiques, HTC Home Store, Hayseed, R. Derwin Clothiers, Sister Parish Design (by appt. only)
In New Preston: The Smithy Market, Plain Goods, New Preston Kitchen Goods, J. Seitz & Co.
In Washington: George Home, Hickory Stick Bookshop, Pinnacle, The Huntress Gift Shop at The Mayflower Inn
farms, parks & scenic stops
Hogan’s Cider Mill in Burlington is a stop we make on our way to Litchfield. This roadside market offers hard cider, regular cider, cider donuts, a gift shop, and fall harvest for sale. On weekends, they have food trucks too. It’s a fun stop for the family.
Thorncrest Farm in Goshen is another favorite stop. You can visit with the dairy cows in the barn, and indulge in their milk house chocolates. They are delicious!
Averill Farm & Orchard in Washington offers a u-pick apple orchard, pumpkins and gourds, and farm fresh goods in their market.
Mount Tom State Park in Litchfield is a great place to hike and get water views with your fall foliage. The view from the tower trail is one of the best in Connecticut. The grounds around the pond is a popular picnic spot to enjoy after your hike.
Topsmead State Forest in Litchfield has an idyllic tudor style mansion estate on the property along with gardens and woodland hiking trails.
Hidden Valley Preserve in Washington Depot has extensive wooded hiking trails with lookouts, and pretty fall foliage views on the Thoreau Bridge. We’ve hiked this one a lot with our boys.
Kent Falls State Park in Kent has a large cascading waterfall and a covered pedestrian wooden bridge at the entrance to the park. We’ve done this hike along the falls with our boys a few times. I like it best in the fall and winter. It’s a stunning large waterfall with big cascading falls.
The West Cornwall Bridge in Cornwall is one of the only operational covered bridges remaining in Connecticut stretching over a rambling part of the Housatonic River. It’s a peaceful place to visit with pretty river views. The drive along the Mohawk Trail once you cross the bridge is lovely in the fall too. It’s one of the three historic covered bridges still standing in Connecticut. The other one in the Litchfield Hills is the Bulls Bridge in Kent.
I’ll update this guide as we discover new places to love in the Litchfield Hills.
Last updated October 2025.