How to Spend an Autumn Afternoon in Litchfield, Connecticut

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:

  1. About Litchfield, Connecticut
  2. What to do in Litchfield, Connecticut
    1. Take a walk on West Street—and don’t miss Cobble Court.
    2. Learn some local history at the Litchfield Historical Society.
    3. Tour Tapping Reeve House & Law School, America’s first law school.
    4. Grab lunch at The Village.
    5. On your way out, visit the Lourdes at Litchfield Shrine.
    6. Other Things to Do in Litchfield, CT
The post office in Litchfield, Connecticut

What to do in Litchfield, Connecticut

Take a walk on West Street—and don’t miss 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 in Cobble Court, Litchfield, Connecticut
Cobble Court Litchfield Connecticut

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).

Litchfield Historical Society Connecticut
Litchfield Historical Society

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.

The Tapping Reeve House, America's first law school, in Litchfield, Connecticut
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Grab lunch at The Village.

After a few hours of sightseeing, head back to West Street for a local pint and fish & chips.

The Village Litchfield Connecticut

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
Lourdes in Litchfield Shrine Connecticut
Lourdes in Litchfield Shrine Connecticut

Other Things to Do in Litchfield, CT

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. Litchfield Distillery has a strong regional following, as well as the local vineyards along the Connecticut Wine Trail.

For those who love the outdoors, Kent Falls State Park is less than 30 minutes away

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.

West Street Litchfield Connecticut
South Street Litchfield Connecticut
West Street Litchfield Connecticut

West Street greenery Litchfield Connecticut
West Street Ollie's Pizza Litchfield Connecticut
Litchfield Connecticut Town Hall
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South Street Litchfield Connecticut
West Street Litchfield Connecticut
What to do in Litchfield, Connecticut by Mia Lupo

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A Francophile based in coastal New England

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