A WEEKEND IN LITCHFIELD COUNTY
For design enthusiasts, food lovers, and a little time outside.
When we bought our cottage in Falls Village earlier this year, we’d only been to the northwest corner of Connecticut a handful of times—usually just passing through on the way to the Berkshires or for an afternoon in New Preston. Those quick trips never gave us the full picture of Litchfield County’s charm.
We closed on Pennybrook Cottage in March and spent the next few months getting it ready for guests, and in the process, got to know the area ourselves. What we found was a mix of rolling farmland and storybook villages, layered with a surprisingly rich design scene and restaurants that feel more ambitious than you’d expect for such a quiet corner of the state.
Litchfield County still feels like a bit of a secret, even after a nod from Condé Nast Traveler as one of the “Best Places to Go in the US for 2025.” I’m always surprised by how many New Yorkers or East Coasters have never heard of it.
After many weekends driving to and from the cottage, trying new restaurants, and poking into every design shop I could find, I’ve pieced together what feels like the perfect weekend itinerary. It’s part design pilgrimage, part small-town wandering, with plenty of good food in between. If you’re curious where to start, and you’re into design, food, and idyllic New England scenery, here’s how I’d spend three days in Litchfield County.
FRIDAY
Make your way up Route 7 with a stop in New Preston. It’s tiny, but packed with good shops:
Plain Goods for elevated basics and homewares in a perfectly restored colonial
Privet House for tabletop, scents, and interiors books you’ll want to take home
Pergola for house plants, pottery, and garden tools with patina
J. Seitz & Co., a local staple with everything from sheepskin throws to cashmere sweaters (but especially don’t miss the back deck with waterfall views)
Eleish Van Breems Home for a collection of Scandinavian furniture and objects
Grab lunch on the covered patio at The Owl—their potato pizza is a must.
Then walk down the street to Smithy’s Market, which is housed in an old blacksmith shop and filled with local produce, prepared foods, and pies. I like to pick up flowers or something for the fridge at the cottage.
Plain Goods & Smithy’s Market
From there, head north to Falls Village. The drive is quiet and scenic. Check in at Pennybrook, take a beat to settle in, maybe sit outside for a bit.
Later in the afternoon, head to Millerton (about 15 minutes away) for a treasure hunt at Montage Antiques. They are constantly restocking amazing European antiques at fair prices. They close at 5, so leave yourself enough time to browse. Afterwards, walk down the street to Willa for a glass of wine and a snack at the bar.
Head back to Falls Village and walk from the cottage to Falls Village Inn, where you can sit on the patio with the rest of the small town and order a burger or fish & chips. It’s casual and local in the best way.
SATURDAY
Start with coffee and a pastry at Blue Gate Bakery. They bake everything in-house and sell out fast on weekends. Their ham and cheese croissant is amazing.
If you're in the mood for a little movement, hike the Pine Knob Loop Trail. It’s about 2.5 miles and has great views at the top. Or rent an e-bike at the West Cornwall Covered Bridge and ride along the river.
Back in West Cornwall, visit Michael Trapp’s shop. It’s a layered mix of antiques, garden pieces, and objects with a collected-over-a-lifetime feel. You’ll either walk out with a vintage urn or wish you had.
Stay for lunch across the street at The Pink House, just steps from the bridge. Sit outside if the weather’s nice.
Michael Trapp, the Covered Bridge, and the patio at the Pink House
Michael Trapp, the Covered Bridge, and the patio at the Pink House
In the afternoon, head back to Falls Village and walk down Main Street to browse:
100 Main for art and handmade objects, curated by Bunny Williams
Marché for French antiques and smaller vintage finds
John Robshaw’s shop, a little up the road, for block-printed everything in his signature colors and patterns
Later in the day, head down to Litchfield. Park near the green and walk around town—Milton Market is always worth a stop for housewares and gifts. If you’re hungry, grab a drink and something small at Lost Fox Inn. For dinner, book in advance but try Arethusa al Tavolo (highly raved about CT foodie destination) or Materia (Italian, a little quieter).
Milton Market, Lost Fox Inn
SUNDAY
Take the short but scenic drive up Salmon Kill Road towards Salisbury. Grab coffee at Sweet Williams Coffee Shop & Bakery.
On your way out of town, swing through Kent and walk Main Street. It’s postcard-y in the best way. RT Facts at Kent Barns is a must (incredible antiques and salvaged finds. Hit Woodford’s General Store on the way out.
Finish with a stop in Sharon. Browse the beautifully curated collection of homewares at The McKenzie Shop, then grab brunch or lunch at Le Gamin, a low-key French café with sidewalk seating.
When you’re ready for a weekend away, this loop makes a pretty solid plan. And (biased opinion) Pennybrook Cottage is the perfect home base.