What do the literary classic “Uncle Tom’s Cabin” and Broadway musical “Hamilton” have in common? They both have ties to one of New England’s dreamiest getaways: Litchfield. First incorporated as a town in 1719, this storied Connecticut gem is home to the first law school in the U.S., with Vice President Aaron Burr — a key character in the “Hamilton” musical — notably being the school’s first pupil. Another important Litchfield resident, writer Harriet Beecher Stowe, spent her whole life in Connecticut, where she wrote her masterpiece “Uncle Tom’s Cabin.”
In Litchfield, the old and new go hand in hand. Its Bauhaus-inspired architecture makes it a hub of Modernism in Connecticut, second to neighboring New Canaan. Once you have soaked in the history and architecture, the town also boasts a wealth of parks and natural beauty on its doorstep, where you can embark on tranquil hikes filled with nature’s colors and sounds.
For old-time nostalgia and countryside serenity, there’s no better place than New England. The fall season’s rusty orange, golden, and maroon hues may have made the region famous, but there is so much more to New England than its iconic fall destinations with leafy views, and Litchfield is a prime example.
Litchfield is an easy trip from the bustling and underrated Connecticut capital city of Hartford, located just 32 miles away. If you are hungry for more small-town charm, you’re in luck. Around 20 miles outside of Litchfield is New Hartford, a cute town full of antique shops and rolling hills.
Litchfield’s historic buildings exude timeless charm
Litchfield’s abundance of historic buildings enliven the town center with century-old charm. The Litchfield History Museum takes you on a journey through the town’s evolution, from the early 1700s when the Tunxis Native American tribe lived on the land to the present day. The museum hosts a collection of early American artifacts, extensive historical archives, and fascinating exhibits. Entry to the museum is free, but remember to check the website before visiting as it is only open seasonally starting in mid-April.
There is no better way to experience Litchfield’s timeless charm than by strolling the quaint streets of the Litchfield Historic District, a designated National Historic Landmark. Along South Street, you will see many excellent examples of old-school New England architecture dating back to the 1700s. As you amble on the leafy shaded street, you can admire the many Greek and Colonial Revival structures with storied pasts. The Tapping Reeve House was once home to America’s oldest law school. Inside, you can step into the shoes of a 19th-century law student and visit a classroom re-created to look just like the original. A few steps away is the stately Seymour Cunningham House, a classic example of the Colonial Revival-style vacation homes favored by wealthy residents in the early 1900s.
Litchfield’s list of historic buildings is long enough to fill a couple of days of exploring, but the town center is full of modern-day boutiques, restaurants, and cafes that you’ll want to make time for. Stop for a beverage and Italian treat at Espresso 59 on the Litchfield Green, and spend a night at the Lost Fox Inn, a 1740s tavern transformed into a chic boutique hotel just outside of town.
The best hikes near the Litchfield town center
