Originally published on October 8, 2019, this post may have been edited for clarity or updated with new information.
Now that I’ve begrudgingly accepted that fall has arrived, I want to make more of an effort to explore different parts of Connecticut beyond the Gold Coast.
I took a day to drive from Fairfield County to Litchfield during Columbus Day weekend.
About Litchfield, Connecticut
Litchfield, Connecticut, is a historic New England town located an hour away from southern Fairfield County, CT, and two hours outside of New York City. It’s an easy drive to change up the scenery and enjoy the fall foliage without driving further out to New Hampshire or Vermont.
The town, which celebrates its 300th anniversary in 2019, is a prime example of a beautifully preserved 18th-century American village.
Autumn marks the height of tourist season in Litchfield because of its elevated and expansive views of fall foliage. The town offers warm hospitality for the many out-of-towners enjoying the scenery and exploring the area.
Downtown Litchfield is very walkable and pedestrian-friendly—and it would take an effort to get truly lost. If you’re visiting for the afternoon, here’s a quick hit list of things to do and see in town:
- About Litchfield, Connecticut
- What to See and Do During a Day Trip to Litchfield, Connecticut
- Additional Activities in Litchfield, CT
- Where to Stay in Litchfield, Connecticut
What to See and Do During a Day Trip to Litchfield, Connecticut
Take a walk on West Street and Cobble Court.
It’s clear that the restaurants and storefronts along Litchfield’s main street take pride in keeping up their quintessential New England image. Nearly every window and stoop is decorated for the season, waiting to be photographed by tourists.
Milton Market is a beautifully curated general store and apothecary, and was named one of the Top 25 Best Home Stores in America by House Beautiful.
Address: 14 Cobble Ct, Litchfield, CT 06759
Learn some local history at the Litchfield Historical Society.
It’s fitting that the current exhibits—Sold, Made, & Grown in Litchfield and Litchfield: The Making of a New England Town—focus on a rich cultural overview of Litchfield’s history in celebration of its 300th anniversary. Free admission (donations may be made at the door).
Address: 7 South St, Litchfield, CT 06759
Tour Tapping Reeve House & Law School, America’s first law school.
The Tapping Reeve House, which also belongs to the Litchfield Historical Society, recently recreated natural grounds that would be representative of the 18th century.
Address: 82 South Street, Litchfield, CT 06759
Grab lunch at The Village.
After a few hours of sightseeing, head back to West Street for a local pint and fish & chips at The Village, a community anchor off the Litchfield Green since 1950.
Address: 25 West St, Litchfield, CT 06759
On your way out, visit the Lourdes at Litchfield Shrine.
I’ll be the first to admit that I’m not the most devout Catholic, but this Connecticut replica of the original Lourdes shrine in France is a special community treasure:
The Shrine of Lourdes in Litchfield is a replica of the Grotto Lourdes in France. Built of local fieldstone by two Montfort Brothers, Brother Alfonso and Brother Gabriel, with the help of Montfort seminarians and people from the area, the Shrine was dedicated in 1958. The Montfort Missionaries developed the Shrine so that individuals, families and groups could come to pray, to reflect on their own lives, and to imitate Mary’s life of faithful discipleship.
– The shrine of lourdes in litchfield
Address: 83 Montfort Rd, Litchfield, CT 06759
Additional Activities in Litchfield, CT
Schedule tours and tastings at Litchfield Distillery or along the Connecticut Wine Trail
I would love to come back to Litchfield again this fall. There are several other attractions to check out in Litchfield and the surrounding area, but if we’re being honest, most of them will require a designated driver—or better, an overnight stay.
Litchfield Distillery has a strong regional following, as well as the local vineyards along the Connecticut Wine Trail. In recent years, the Connecticut Wine Trail has expanded across the state as local entrepreneurs invest in wine tourism in the Nutmeg State.
Hike Kent Falls State Park
For those who love the outdoors, Kent Falls State Park is less than 30 minutes away. Walk across the covered bridge, and you’ll see the beautiful natural falls pouring into the Housatonic River.
If you’re looking for a change of scenery outside of the New York City metro area, I would recommend getting in the car and heading to Litchfield for a view of rolling hills, a brisk stroll along the brick sidewalk, and a local conversation over a hot, spiked cider.
Where to Stay in Litchfield, Connecticut
With the new additions of hospitality properties in downtown Litchfield, it’s much easier to plan a weekend getaway in the area.
The Abner Hotel
Uniquely located in the former courthouse, The Abner Hotel is a vibrant, lively addition to downtown Litchfield. The Verdict:, the hotel’s rooftop bar, embodies the fresh, new perspective of the sleepy Connecticut village.
The hospitality group behind The Abner Hotel, SALT Hotels, has already proven itself in New England with sister properties The Salt House Inn and The Brant, both based in Nantucket, MA.
Bonus: If you’re looking to return in the winter, the hotel’s Ski & Stay package includes two lift tickets to nearby Mohawk Mountain.
Address: 15 West St, Litchfield, CT 06759
Belden House
A short walk from West Street brings you to Belden House & Mews, a restored landmark complete with dining, wellness, and thoughtful amenities. The 50-foot pool is a welcome surprise during the summer months for hotel guests looking to disconnect and relax in nature.
The Belden House’s larger sister property, Troutbeck in Amenia, NY, is a 40-minute drive away, but well worth visiting for dinner or booking a separate trip.
Address: 31 North St, Litchfield, CT 06759
The Litchfield Inn
The most established hotel in Litchfield, The Litchfield Inn is the perfect place for weddings, corporate retreats, events, and larger parties.
The property is committed to keeping up with the newcomers and has announced that it will open an outdoor pool in Spring 2026.
Address: 432 Bantam Rd, Litchfield, CT 06759
New England Parisienne 