Five of the Most Charming Shops in the USA, According to Tom of Homestedt
A shopkeeper and designer on the most charming stores he returns to again and again
This winter we’re starting a new rhythm in Escape Club: every other week, we ask someone with real experience or insight to share a quick “Top 5” from their world — design, hospitality, food, nature, and the quieter corners of culture that shape how we travel. It’s a chance to hear directly from people who actually live and breathe these places, and a small bonus for our paid subscribers.
We kicked off the series with Casey Scieszka — writer, innkeeper, and co-owner of Spruceton Inn — who shared her Top 5 motels across the U.S., drawing from years spent restoring, running, and reimagining one herself.
For this installment, we’re turning to someone whose work is rooted in the idea of home — and all the details that make it memorable.
Ask a Shopkeeper: Tom from Homestedt Shares His 5 Favorite, Most Charming Shops in the USA
Tom Roberts is no stranger to charming shops. As the co-founder of Homestedt, a design-led retail and development studio based in Livingston Manor, his work sits at the intersection of thoughtful design, historic preservation, and everyday livability.
Alongside his wife and partner, Anna Åberg, Tom has helped shape some of the Catskills’ most quietly influential spaces — from the renovation of hospitality projects like Seminary Hill’s Boarding House, to the development of Homestedt Houses, and the restoration of the historic North Branch Cider Mill, where Homestedt expanded its retail vision even further.
Most recently, in fall 2025, they opened the Homestedt Barn just across the driveway from the Cider Mill. Inside, the barn offers a carefully sourced mix of antique wares, furniture, and home goods — a natural extension of Homestedt’s belief that a home is built through small, meaningful details collected over time. Naturally then, when they opened the space, they did so with another of the areas experts in home – Jersey Ice Cream Co. – featuring a collection of furniture sourced from England and Scandinavia.
Below, Tom shares five of the most charming shops in the U.S. – places he returns to for inspiration, delight, and the simple pleasure of discovering something well made.
Some highlights: three shops within easy reach of NYC, one further-flung stop where shoppers are greeted with hot chocolate and waffles, and a cheese store in Charleston where, as Tom puts it, “you could be forgiven for thinking you were in Paris — except the staff here are very friendly.”
Last, for those still doing their holiday shopping, be sure to check out what Homestedt gift made WSJ’s “We Wish You a Very Specific Christmas” feature this year. It’s since sold out, but there’s still plenty of whimsical, Upstate-appropriate gifts, made easy to browse via Homestedt’s own Holiday 2025 Gift Guide + 50 Gifts Under $50 list.
Enjoy — and if this series resonates, feel free to hit reply or leave a comment. As always, we’d love to hear which worlds, people, or perspectives you’d like us to explore next.
Stay warm out there, and Happy Holidays!
-Erin