Little towns dot the map of the Catskills Mountains. Most towns are no more than a stop light, gas station, and corner store, but there are plenty of small towns with big personalities brimming with cafes and cute shops.
In this guide, we’ll be exploring towns in Sullivan County. This county covers the southwestern region of the Catskills straddling the border of New York and Pennsylvania. Admittedly, Sullivan County is known for its trout fishing culture over its art scene. But, we’re changing that one blog post at a time.
The pandemic led to a boom of Brooklynites moving to the Catskills to open cool design and vintage shops. It also brought a wave of culinary gems and fancy hotels to the region.
We’re visiting Sullivan County for the eclectic shops featuring secondhand stuff, art, and home goods (Sorry, trout fans). This is a real girl’s girl guide that prioritizes bopping around to places with sweet treats and trinkets. We’ll start in Callicoon and work our way to Livingston Manor. You could follow this guide backward and start with brunch at The DeBruce (but more on that later).
While there are bigger towns in the area like Liberty and Monticello, the three towns featured in this guide have a small-town charm that you can’t beat.
Let’s get into it.
From town to town
Callicoon
Get ready to shop vintage, home decor, and more in Callicoon. Most of the shops are along Lower Main Street. There is a parking lot with plenty of spots by the railroad tracks between Lower Main Street and Upper Main Street.
The best vintage shops to visit are Lee Hartwell Antiques for mid-century modern decor plus eclectic jewelry finds and Ragtime Clothing Exchange for true vintage clothes.
Across the street, Callicoon Vintage has great 70s vibes with artful furniture pieces and a great vinyl selection. Pao! is another good secondhand shop with more contemporary clothes like BDG jeans and chunky sweaters at reasonable prices.
Don’t miss Spruce Home Goods down the alley for kitchenware, gourmet pantry items, and home goods. At the counter, they also sell baked goods to get your sweet treat fix.
Outside of town, you can make a stop at Seminary Hill for a cider or a bite to eat.
Pit Stop: North Branch
From Callicoon, take North Branch Road to Roscoe. The town of North Branch has nothing special going on except for North Branch Cider Mill, a red barn building that has been reimagined as a home goods store and candy shop. North Branch Cider Mill is the best shop you’ll visit on this itinerary if your idea of the best shop has apple cider donuts, cookbooks, and kitchen tools. (As ThatPlannerFriend, it checks all my boxes.)
The team behind the popular Homestedt shop in Livingston Manor opened North Branch Cider Mill, and, honestly, it’s way better than the original shop. Buy some goodies like candy and apple cider and hit the road again.
Roscoe
A sign that says “Trout Town USA” welcomes you to Roscoe. This tiny town has a couple of standout shops that are worth the stop.
Our favorites were The Hound Books on Union St. and Taylor + Ace on Stewart Ave. These two streets are on the same block, you just need to do a loop. The Hound Books is a bookshop with new and used books with a real-life hound dog mascot that wanders around the store. Taylor + Ace is a well-curated vintage shop with amazing home decor at great prices.
Because we couldn’t resist a sweet treat, we stopped into the Spotted Cow Cafe for Greek and Middle Eastern-style pastries like baklava.
Livingston Manor
Last but not least, visit Livingston Manor, the largest of the three towns. Although Main Street looks long on the map, the action happens on Main between Kaatskeller Pizza and Pleasant St.
The most important stop on your trip to Livingston Manor is the Catskill Art Space. This free museum hosts world-renowned artists like James Turrell with rotating exhibitions. It’s a small two-story space but it packs a lot of art.
Along Main Street, there are a couple of shops to explore, but by this point you might be shopped out like we were.
Grab dinner at Kaatskeller, one of the restaurants in the area. This elevated pizza spot serves (you guessed it…) pizza and other dishes like (another shocker…) trout. The space is a vibe with a cool bar on the second floor. During the summer peak season, there will probably be a long wait and they don’t take reservations. Other great options to hang out nearby are Upward Brewing Company and Catskill Brewery.
You could do this itinerary backwards starting at Livingston Manor. If you’re visiting Livingston Manor in the morning, I can’t recommend brunch at The DeBruce enough. It’s a little ways from Main Street into the countryside but it’s one of the best brunches I’ve ever had.
Where to stay
All of these towns have plenty of cabins in the surrounding mountains to rent on Airbnb and VRBO. We stayed in Jeffersonville (about 20 minutes from Livingston Manor) at Hill House on Hubert. We chose this location because the cabin had a sauna. The town of Jeffersonville also has some hidden gems like Jeffersonville Bake Shop and Sullivan Sundries.
I would not recommend a day trip to Sullivan County from New York City. It takes about 2 to 2.5 hours to drive from NYC, which means you’ll be in the car for more than half the day. The Catskills is a great weekend trip to relax and explore all the towns outlined in this guide.
Good to knows
The ideal time to visit these towns is on Saturday when stores are open for longer hours. Many of these shops may be closed during the week, so Saturday offers the best opportunity. Keep in mind that most stores close by 5 p.m., so to make the most of your day, plan to head out by 11 a.m.
This is just one detailed day of a girl’s getaway I spent in the Catskills with friends. For a full guide on planning a well-deserved wellness weekend for the girls, click here.
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