A guide to the small towns of Hudson Valley and the Catskills (2024)

You don’t have to get too far outside of New York City—30, maybe 40 miles—before the landscape changes. Dense urban areas and suburban strip malls grow fewer and farther between, and a more bucolic New York emerges. All around the Hudson River, and farther inland toward the Catskill Mountains, quaint little towns (some of which are so small that they’re barely towns at all) beckon weary city dwellers seeking a respite from the chaos of New York.

If you’re reading this, you’re probably one of those people—and if so, this guide is for you. Whether you want to commune with nature, explore the history of the region, or just chill for a weekend, we’ve found a spot for you.

Here, we’ve outlined the best things to do in five small towns in the Hudson Valley and the Catskills—particularly outside of Beacon and Hudson, two well-known destinations that have seen a boom in tourism in the past few decades.

Catskill

Visit if: You spend almost every Saturday at the Met

“Must I tell you that neither the Alps nor the Apennines, no, nor even Aetna itself, have dimmed, in my eyes, the beauty of our own Catskills?”

American painter Thomas Cole heaped that effusive praise on the Hudson River Valley in 1842, and while the landscape has changed dramatically in the years since, some of the pastoral beauty that inspired Cole can still be found in his adopted home of Catskill.

The small town, located about 120 miles north of New York City, is situated between the Hudson River and the Catskill Mountains—and Cole’s home just outside the center of town, known as Cedar Grove, has stunning views of the latter. It was here that he helped create the Hudson River School, the 19th-century movement that cemented American art as a force to be reckoned with.

Today, Cole’s house and studio is a museum and National Historic Site dedicated to his life and to the legacy of the Hudson River painters. Visit today and you’ll see the studio where he created some of his most enduring works, as well as the landscapes that inspired him. It also serves as a gateway to the Hudson River School art trail, with more than a dozen sites dotted throughout the region.

But it’s not the only reason that arts aficionados should plan a trip to Catskill; the town is a bustling creative hub, with a bevy of galleries and shops lining its charming Main Street. (Check out the Village Common for locally produced candles and home goods, or Open Studio, a gallery-cum-studio space owned by two local artists.)

There’s more on the horizon, too: Lumberyard, a waterfront arts venue and residency space, is poised to hold its first performances this summer; and nearby, artist Stef Halmos is in the process of transforming an old warehouse into FORELAND Catskill, a new contemporary-arts center. Soon, Catskill may be giving neighboring art destinations like Hudson and Beacon a run for their money.

See Also

Winter Activities in Bend, Oregon You Need to Try - Lauryncakes12 Unforgettable Places In Missouri That Everyone Must Visit This WinterThe Best Tubing and Sledding near the Bay Area - 510 Families10 Fun Things to do in Nebraska with Kids in 2022

Millerton

Visit if: You’re a regular at estate sales and the Brooklyn Flea

If you’re the sort of person who gets really excited by antique furniture and other vintage goods, chances are you’ve visited some of the better-known flea markets north of NYC—places like the massive outdoor market in Brimfield, Massachusetts, or the 600-vendor-strong Stormville Airport flea in Dutchess County.

The tiny town of Millerton—located in Dutchess County, just about a mile from the New York–Connecticut state line—is hardly considered off the beaten path at this point. Though it’s less frequented than those destinations, or even Hudson, often considered the hub of upstate antiquing, its shops are often aimed at a very specific, and very design-minded clientele.

In Millerton, you’ll find both high-end stores whose selection is expertly curated and arranged to a T and plenty of places where the shopping experience is more akin to rummaging through your quirky aunt’s basem*nt—you don’t quite know what you’ll find, but you know it’s bound to be interesting.

Shopping at the Millerton Antiques Center, located smack in the middle of the town’s Main Street, is more like the latter. It’s been a staple for over 20 years, and now sells an eclectic assortment of goods from more than 30 vendors. On a recent visit, we stumbled across items you wouldn’t spare a second glance—old photographs, piles of tarnished silverware, random landscape paintings—along with plenty of vintage gems, like a Russel Wright-designed casserole and dishes by Paul McCobb. It’s one of those places where the hunt, and peeking into corners stuffed with all sorts of weird or cool old things, is part of the fun.

Montage, also located on Main Street, is more of the former. The shop sells a little bit of everything, but there’s a focus on furniture—a mix of midcentury modern, 19th-century formal, and rustic pieces that wouldn’t look out of place in a barn—and lighting, with the occasional objets d’art thrown in. It’s next door to Hunter Bee, which also has a more curated selection, but with a twist. Owners Kent Hunter and Jonathan Bee opened the shop a decade ago and bring their unique perspectives to the shop’s selection: Drawing from their previous lives as a creative director and multimedia artist (respectively), the duo might showcase a six-piece Danish dining set or an ornate decorative mirror that looks like it belongs in a Victorian drawing room. One thing’s for sure: It’s almost impossible to leave this town empty-handed.

See Also

12 Best Things to do in Helen, GA

Kingston

Visit if: You’re over Hudson’s hipster vibes

History isn’t in short supply in Kingston, a city of about 23,000 that’s about 100 miles north of New York City. One of its most popular intersections, Four Corners, is allegedly the only spot in the entire country where each corner is occupied by a pre-Revolutionary War building. And the former state capital is home to no fewer than four historic districts, each of which has its own flavor and its share of lovely old buildings.

But in the past decade or so, Kingston has experienced a renaissance. Though it’s not as well-trod by weekenders, it has plenty of cool shops (including an abundance of excellent second-hand stores), restaurants, and cultural offerings. That mix is perfect for those who want to experience small-town charm while still getting their fix of urbanist-friendly hot spots.

One thing to know about Kingston is that spending a day in the city isn’t as simple as sauntering down a central Main Street; it has a distinct uptown and downtown, each with its own mix of shops, architecture, and other cool things to check out.

Uptown, which is closer to Esopus Creek, is where you’ll find the Stockade Historic District, which includes the famed Four Corners (one building is now home to Rough Draft, a stellar bookstore-bar hybrid) and the circa-1852 Old Dutch Church, a community landmark.

Along Wall Street, uptown’s main stretch, you’ll find businesses that have brought a bit of new-world hipness to Kingston. BSP, a club that opened in a former vaudeville theater more than a decade ago, has hosted bands like Grizzly Bear and Television; nearby, Rocket Number Nine is an excellent spot for crate-diggers in search of vintage vinyl. Wall Street is also where you’ll find the Hudson Valley LGBTQ Community Center, which recently took to the street—literally—and painted the crosswalk in front of its HQ with the LGBTQ and trans pride flags.

Downtown, meanwhile, is home to the Rondout, another historic district that’s a reminder of the city’s past as a “thriving maritime village,” as the Friends of Historic Kingston puts it. Close to Rondout Creek, this part of town is home to the Hudson Maritime Museum—worth a visit if you want a deeper dive into the waterfront’s industrial past—as well as a collection of 19th-century buildings that were once used for manufacturing.

Now, many of those spaces have been repurposed into trendy restaurants and shops. A bunch have popped up on Broadway, including Hops Petunia, a flower shop that sells handmade pottery, soothing candles, and other home goods, and Clove & Creek, a coffee shop that also peddles items for the pantry and outdoors. One of the most popular spots in the area is Brunette, a homey wine bar where you can grab a bite to eat—a perfect way to end a day of exploring.

Phoenicia

Visit if: Your hiking boots get more use than your sneakers

The hamlet of Phoenicia may be tiny—its population is just around 300 people, according to the most recent census data—but it’s hefty on the outdoor offerings thanks to its unique position within the Catskills. It’s close to several natural wonders (including Hunter Mountain and Kaaterskill Falls), and Esopus Creek runs right through the center of town. .

That waterway was once an industrial artery lined with mills and loggers; now, it’s a bustling spot for tubing and fishing. The Town Tinker Tube Rental is the spot in town for those looking to get out on the water: They rent tubes, life jackets, and other equipment. But if you’re new to tubing or hoping for more of a chill, lazy river vibe, this may not be for you. The company notes that tubing on the creek “is not a man-made amusem*nt park ride”—instead, it’s more like whitewater rafting, with all of the dips, bumps, and obstacles that entail.

Phoenicia also has two campgrounds—Black Bear and Sleepy Hollow—that abut the Esopus, with the former closer to Town Tinker, and the latter on the other side of town.

But if you’d rather stay on dry land, there are a number of hiking trails, with varying levels of difficulty, that are easily accessible from Phoenicia. The Tanbark Trail, a 2.3-mile loop, begins close to the center of town and takes intrepid hikers more than 1,100 feet above ground level. (Bring water, and wear good hiking shoes.) Signs along the trail direct you to points of interest, including the Phoenicia Overlook, a scenic viewpoint that has views of the town and the mountains beyond.

No trip to Phoenicia is complete without a visit to the Phoenicia Diner, whose tote bags and T-shirts you’ve surely seen around New York City. (Eater NY’s Robert Sietsema posited, in 2016, that it’s the ultimate “hickster” restaurant—i.e., “hipsters who move upstate become hicksters.”) It’s become a popular destination for both weekenders driving through the Catskills and those who call the area home, and for good reason: Its modern-day diner classics (tuna melt, omelettes, and the like) are hearty, delicious, and affordable—just the kind of food you want after a day spent tubing or hiking.

Stone Ridge

Visit if: You’ve binged every episode of Restoration Home

There’s no shortage of quaint towns filled with historic houses in the Hudson Valley and the Catskills, but Stone Ridge, a tiny hamlet in Ulster County, is especially picturesque—particularly if you’re a fan of old stone houses, a dominant vernacular building type in the region, and one that’s in abundance in Stone Ridge.

Though Dutch settlers lived in the area in the late 17th century, it wasn’t until the years immediately before the Revolutionary War that some of the town’s oldest structures—such as the Cornelius Wynkoop House, a circa-1767 home made from gray limestone that’s notable for having once hosted George Washington—were built. Now, many of those are part of the Main Street Historic District, which stretches along much of Route 209 (the main thoroughfare through town) and is listed on the National Register of Historic Places.

Alas, many of Stone Ridge’s most exquisite properties are private homes—some of which are on the market for upward of $1 million—but there are a few historic buildings that let the public in. One of the most spectacular is the Hasbrouck House, built as a country estate in the 1750s and recently renovated into a 30-room hotel. The property comprises three different lodgings (the main house, a carriage house, and a stable house), and while the rooms themselves have gotten a modern refresh—there’s even an in-ground pool on the premises—there’s no denying that you’re sleeping in a place that has lived many lives. (Despite its name, the nearby 1712 House is actually much newer—and another nice lodging option.)

A slightly more humble structure is the Stone Ridge Library, also on Route 209, which is situated in a stone building from 1798 that originally served as a home; now, it’s a living link to Stone Ridge’s past, one of many that exist in this small town.