Labor Day Weekend in Litchfield: 10 Great Things to Do

Labor Day Weekend in LitchfieldLabor Day Weekend represents the last hurrah of summer for most of us, which inspires a make-the-most-of-it vibe. Litchfield always delivers satisfying experiences for residents and visitors, and these 10 things to do will make the long holiday weekend especially rewarding.

A Walk in the Woods and/or a Walk in Town

Some folks like to walk on trails through Litchfield’s thousands of acres of preserved land, while others prefer strolling along the sidewalks in the historic center of town. There are opportunities this Saturday, Sept. 2, to enjoy either or both.

In the morning, White Memorial’s Director of Administration and Development Gerri Griswold presents her “Loving Haight” guided hike that highlights the “hidden” trails near (the now closed) Haight Vineyard, an area “laced with babbling brooks, towering trees, a bevy of birds, and a view of the vineyard.” Guests are asked to meet at 10 a.m. front of the A. B. Ceder Room at the White Memorial Conservation Center. The guided hike is free but donations will be accepted to help defray the Conservation Center’s programming expenses. See the event page for more.

In the afternoon, the Litchfield Historical Society presents its weekly walking tour, which begins at 1 p.m. at the Litchfield History Museum and lasts about an hour. It’s  a perfect way to explore the town’s celebrated Historic District and discover Litchfield’s vibrant history, including the stories behind famous landmarks, anecdotes about past residents, and an appreciation of prominent buildings.  

The tour is free for historical society members and $10 for non-members. Those planning to attend are asked to register online.

In addition to exploring the rest of the 40 miles of hiking trails at White Memorial, make sure to seek out the trails of the @litchfieldlandtrust, @litchfield_hills_audubon, and @friendsoftopsmead, as well as discovering the trail to the stone tower at Mt. Tom State Park, and the Litchfield Community Greenway.

A Day at the Beach

Labor Day Weekend in LitchfieldLabor Day Weekend is last call to enjoy the public Sandy Beach, located off pretty East Shore Road on the Morris side of the lake. There’s swimming, boating, volleyball, fishing, bathrooms, a picnic area, and even a concession stand. See the website for hours, fees, and other details on visiting.

Goshen Fair

Labor Day Weekend in LitchfieldThe Goshen Fair, one of Connecticut’s major agricultural/country fairs, runs from Saturday through Labor Day (8 am – 9 pm Sat. & Sun and 8 am to 6 pm on Monday) at the Goshen Fairgrounds on Route 63 north of Litchfield center.

Check out the fair’s website to make your plans and don’t miss what’s new this year, including the Dialed Action Sports: Motocross Show and the return after 20 years of the Pork Cook-off Contest.


Hit the Links

Labor Day Weekend in LitchfieldStonybrook Golf on Milton Road has become much more than Litchfield’s 9-hole public course. These days it’s a lifestyle destination. In addition to the course and the golf shop, there’s the new Clubhouse Provisions restaurant, which has been drawing rave reviews. And there’s even music. Mike Wilson will be playing at Clubhouse provisions from 5:30 to 8:30 p.m. every Friday in September. See the Stonybrook Golf website to connect. 

Farmers Markets & Farm Stands

Labor Day Weekend in Litchfield
Litchfield Hills Farm-Fresh Market

The Litchfield Hills Farm-Fresh Market takes place at the Center School parking lot on Saturdays from 10 a.m. to 1 p.m. through late October, before moving to Litchfield Community Center for late fall and early winter.

The Bantam Community Farmers Market, which debuted in June, continues every Friday from 4 to 7 p.m. through October at the Alain White Field on Route 209 in Bantam.

Also on Fridays, Chabad Litchfield holds a Shabbat Market from 5:30-6:30 p.m. at 69 West St. in Litchfield center.

Anyone driving along Route 202 from Litchfield center to Bantam has noticed the Tara Farm stand. It’s one of many farm stands in town, including one at Bunnell Farm on the way to Milton, Winter Winds Farm on Route 63 heading north toward Goshen, and Chanticleer Acres, tucked away off Milton Road on Hutchinson Parkway. Head to our Visit Litchfield CT farms page to discover and connect with more farm markets.

Coffee Culture

Labor Day Weekend in Litchfield
Krafted Brew Lab

Litchfield is a coffee culture haven blessed with coffee shops and scratch bakeries sprinkled all over town – from The Bakehouse in the Old Litchfield Jail, Espresso59, Meraki, and Toast n’ Co. in the center of town to Krafted Brew Lab and Arethusa a mano in Bantam. And that’s just naming some of them! Many are open early, a few stay open later (Espresso59) – and all of them satisfy our cravings. See our website page for coffee lovers page to discover and connect.

Al Fresco Dining

The weather looks perfect for al fresco dining this weekend and Litchfield’s fine restaurants are masters at setting the outdoor mood, whether it’s a sidewalk café lunch at Petraroia Deli on West Street, or lunch or dinner at West Street Green or on the patio at Market Place Tavern in the Old Litchfield Jail. See our outdoor dining page to connect with all of the possibilities.

Road Food Experiences

Labor Day Weekend in Litchfield
Gooseboro Drive-In

Gooseboro Drive-In, or “The Goose” as long fans call it, has offered great roadside burgers, hot dogs, shakes, and banana splits for six decades. Located along Route 202 on the western side of Bantam near Mt. Tom State Park, Gooseboro is open seven days a week until it closes for the season, typically in mid-October. Check the Facebook page and Instagram feed for specials and updates on hours. The address is 1293 Bantam Rd.

West Shore Seafood is a classic roadside stop for fried seafood, lobster rolls and so much more, located on Route 209 above Bantam Lake. Guests come up from the lake, and from near and far, for the fresh seafood, which can be ordered ahead at 860-567-8000, ordered online, or ordered at the counter when you get there.

The only hard part is deciding from so many great choices: clam chowder, lobster bisque, steamed clams, fried calamari, crab cakes, lobster rolls, fish-and-chips, friend clams, and so much more. There are also burgers, chicken sandwiches, hot dogs, and tacos. 

There’s also a retail store with new shipments daily. Call 860-567-8000 to learn more, or check out the websiteFacebook page, and Instagram feed.

Ice Cream & Chocolates

Labor Day Weekend in LitchfieldIs Litchfield the ice cream capital of Connecticut? Food & Wine seems to think so. Those in the know get their homemade ice cream at Arethusa Farm or Peaches N’ Cream, their bespoke gelatos at Espresso59, and their soft serve and Sundaes at Gooseboro Drive-In.

For gourmet chocolates, head to the hometown Litchfield Candy Company, or take a short and pretty ride across the border to Goshen and discover Milkhouse Chocolates at Thorncrest Farm. See our resources page for more info.

Whiskey & Spirits

Litchfield Distillery offers complimentary tours and sample tastings of its award-winning spirits, arranged by reservation on the website. Walk-ins are welcome if a time slot isn’t full. Tours are offered on the hour beginning at 11a.m. The last tour begins at 4 p.m. on Saturday and 3 p.m. on Sunday. In a Facebook post this week, the distillery said reservations are filling up fast, “so we encourage you to book your complimentary tour & tasting soon!” You can do that here: (Litchfield Distillery is closed on Labor Day but open normal hours Sat. & Sun.)