Are you seeking a tranquil and effortless escape just three hours away from New York City? Our new “Three Days In” series for local jaunts kicks off in the gorgeous Catskills—perfect for uncrowded mountain air, eclectic antiquing, laid-back Main Streets, and impromptu discoveries. Here’s how our weekend went down (and how to recreate it for yourself):
Your Guide to Three Days in the Catskills
Day 1: Arrival, Settling In & Exploring Windham
Fresh from city traffic, we rolled into our Airbnb near Windham just in time for a leisurely late lunch on the back porch (pro tip: bring prepped meals from A&G Fine Italian Foods and groceries from Wegmans—you’ll thank yourself). We were able to quickly get into the relaxation mode because we didn’t have to go hunting for a supermarket or restaurants nearby. Additionally, we didn’t need to conduct any research prior to our trip, making it effortless to choose meals from familiar locations. We took enough food for a couple of days.
If you’d rather stock up locally, Hickory Hill Market in Windham is a treasure: think gourmet groceries, bakery, pizza shop, a deli with beautiful olives, and even a beer cave with every variety imaginable. It’s on the expensive side, and the variety of prepped meals is very limited. Plus, it may not be as local depending on where you stay. Everything in this area is a bit of a drive.
The afternoon called for a mellow town wander, popping through Windham’s Main Street. If you prefer hotels over Airbnbs, Windham’s boutique options are year-round stunners—think classic Catskills timber, chic interiors, and prime locations. Some top spots:
The rest of the day? Breezy drives and soaking up that small-town pace. We settled in early, gazing at the mountains and raising a toast to not having to grocery shop today.
Day 2: Antiquing Adventures & Main Street Magic
A cloudy morning was perfect for a lazy breakfast at “home”—then, armed with coffees, we hit the legendary Catskills antique trail. First stop: Tannersville, where main street is a colorfully painted mural come to life, packed with indie shops, and home to the Tannersville Antique & Artisan Center.
Don’t miss:
- Blue Barn Marketplace (Shandaken)
- Rustic Mountain (Tannersville)
- Rust Diamonds & More (Hunter)
Afternoons in the Catskills are for slow walks and sweet treats. Main street in Phoenicia is so quaint you’ll want to take it slow—be sure to stop at the local pharmacy, Wellness Rx, where the pharmacist was passionate about his customers and his homeopathic remedies (ours whipped up a soothing hand cream just for us after a minor kitchen accident). We bought the cream and enjoyed a wonderful conversation. You can end with a scoop from a local ice cream shop or browse even more collectibles at Small Town Happy before heading back.
Lunch and dinner options are plentiful, from roadside BBQ to cozy taverns.
- Jessie’s Harvest House (Charming, log-cabin vibes)
- Prospect at Scribner’s (Upscale, incredible views)
Need another quaint stroll? Windham’s Main Street has friendly shops and galleries.
Day 3: Roxbury Roads & Unplanned Surprises
We pointed the car toward Roxbury with visions of more antiques at Rick’s—only to find it closed (it happens!). But the Catskills are made for happy accidents: the drive itself was pure magic with rolling hills, sparkling creeks, and charming bridges. In Roxbury, we stumbled onto a tiny eatery (goes with the tiny main street) for bagels and coffee and a sweet little gift shop—all unexpected, all memorable. Sometimes the best finds are the ones you didn’t plan for.
Alternate Activities in the Catskills
- Take a hike at Kaaterskill Falls, or the Windham High Peak Trail.
- Scout for treasures at the Windham Indoor Flea Market or the Catskill Mountain Flea Market (Fridays & Saturdays).
- Visit Hunter Mountain Resort for gondola rides or nearby festivals.
- Explore Saugerties for more antiques, river views, and artisan bakeries.
Where to Stay (Boutique & Airbnb Picks)
- Eastwind Hotel & Bar: Instagrammable Scandinavian style with outdoor saunas and fire pits.
- Albergo Allegria: Old-world charm, top-notch breakfast.
- Hotel Vienna: Cozy, Austrian-vibe lodge with a pool and mountain views.
- Airbnb in Windham: Search for modern-rustic cabins with patios and hot tubs.
Getting Around the Catskills
You’ll need a car—public transit is limited, and rideshares like Uber/Lyft are spotty at best. Parking is free and easy in almost every town. Scenic routes promise gorgeous views between all your stops, so crank up the playlist and savor the drive.
Ready to make your own Three Days in the Catskills? Bring a little flexibility, leave space for serendipity, and prepare to return with a few more antiques and a whole lot of mountain soul.
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