From enchanting forests to upbeat downtowns, from river ports bursting with history to mountaintops revealing glorious panoramas, you’re surrounded by natural beauty, centuries of history, and clever creativity anywhere in the Hudson Valley and Catskill Mountains.
That said, the precise flavors and seasonings of each place are different—sometimes subtly, sometimes dramatically. There’s a lot to be said for choosing a base camp that aligns with your desired vibe and with what you want to do with your time.
That way, from the moment you poke your head out the door in the morning till the end of your day, you can luxuriate in precisely what you’re after.
Less time in the car means more time for soaking it all in. Or maybe you have your base of operations all picked out, but you’d like to take a day trip to someplace with a whole ’nother feel to it. You’ll find loads of opportunities for wildly diverse experiences put together into one journey—without feeling rushed or ending up exhausted.
Then too, just getting from one place to the next leads you through gorgeous terrain sprinkled with quirky surprises. And this time of year, the lovely foliage and crisp fall air envelop the entire Realm like a lovely patchwork of featherweight silk.
So here’s an INSIDER’S GUIDE TO ONE DELECTABLE TOWN IN EACH OF OUR FIVE COUNTIES. Take the time to get to know and fall in love with these places, and you’ll discover more than any one travel guide—even this one!—can possibly capture.
woodstock, ulster county
Maverick Concerts.
Woodstock Town Square.
Woodstock was a music and art mecca long before 1969, with major institutions like Byrdcliffe Arts Colony, the Art Students League of New York, and Maverick Concerts setting up shop here in the early 20th century. They found it beautifuland inspiring, as did the folk and rock musicians who started holding what theycalled Sound-Outs in the mid-’60s. When a young man named Michael Lang andhis friends wanted to organize something bigger, authorities declined—leadingto the big party being held 60 miles away in Bethel but keeping the Woodstockname and dipping its reputation in tie-dye that’s never quite worn off. The town’s largely colonial architecture, surrounded by Catskills forests andlaced with scenic creeks and streams, gives it the feel of an enchanted retreat,which it is. What it’s not is undiscovered; sunny fall weekends draw visitorsto the downtown sidewalks and the village green, home to drum circles and demonstrations.
A perfect fall day in Woodstock might include grabbing lunch at Yum Yum before a hike up Overlook Mountain, where you can soak in one of the finest views anywhere on Earth and contemplate the ruins of a once-luxurious hotel. Back down in town you might spend some time people-watching or grabbing dinner; do try Cucina. Then drive over to the nearby Ashokan Reservoir there’s a lovely rail trail—and you can rent bicycles or opt to visit the nearby Tibetan monastery and visit the monks. Evenings are a great time to see what’s hanging at the local galleries or who’s playing at one of the town’s music venues like the famous Colony. If you'd like to stay overnight, head no further than the boutique Hotel Dylan.
Overlook Mountain. Photo by Jo King.
Overlook Mountain. Photo by Vanessa Villegas.
Ashokan Reservoir. Photo by Gummy Bone.
catskill, greene county
Olana State Historic Site.
Kaaterskill Falls.
Catskill evolved from a teeny village of 10 households at the end of the American Revolution to a bustling port sending hides, honey, and ice downriver. Here, where the Catskill Creek meets the Hudson River, you’ll find a lot of old-school brick preserved in the downtown historic district and glorious views of the river swathed in autumn’s colors from the waterfront parks.
At about 125 miles off Broadway, Catskill is just outside of convenient commuting distance, which keeps it peaceful. It’s a funky, artsy, and resilient little place with creative retail and eateries proudly inhabiting the Victorian facades of Main Street. The largest tidal swamp along the Hudson, RamsHorn-Livingston Audubon Center and Sanctuary, is here; there are trails to walk or paddle, and Audubon naturalists lead guided tours.
Your perfect fall day here might involve a trip to Olana State Historic Site, where Frederic Church lived and painted, followed by a lunchtime picnic on the riverbank. In the afternoon, explore the shops and galleries and/or head to nearby Palenville to take in the glories of Kaaterskill Falls—please obey all cautionary signs. The self-guided Kaaterskill Clove Experience tour offers a unique look at the birth of American art. You can also scoot across the bridge to check out bustling Hudson.
You’ll find elegant choices for dinner and two state-of-the-art performing arts venues. There’s also a lively small-batch brewery and cidery scene with cozy taprooms pouring highly original creations.
Olana State Historic Site.
Kaaterskill Falls.
livingston manor, sullivan county
Olana State Historic Site.
Kaaterskill Falls.
Livingston Manor borrowed its name from the 160,000 acres granted to Robert Livingston the Elder by King George I. In 1880, the hamlet became the highlight and destination of the finest tourist trains on the New York, Ontario and Western Railway. In 1930, a Livingston descendant laid claim to the land and won in court, forcing some residents to buy their own houses from him.
This is the birthplace of the gentle American art of dry fly fishing and the home of the Willowemoc Creek, and you’ll find a museum devoted to the pastime. You’re immersed in the Sullivan Catskills here; Livingston Manor’s nickname of “small town with a big backyard” fits it to perfection.
Get out early, grab some exceptional coffee and an egg sandwich, and watch the morning mist over the Willowemoc. Even if you never get a hook wet, you’ll feel the pull of spending hours on these shores, and the fly fishing museum is the perfect place to understand the people who do that. Then there are the Frick Pond Loop and Willowemoc Wild Forest trails to explore, as well as an array of creative boutiques and gift shops, many of them reflecting a blend of country charm and subtle sophistication. Livingston Manor has its own well-practiced vibe of classic Catskills, wrapping you in the softest flannel and serving you hyperlocal artful food and drink, often accompanied by the soft crackling of a woodstove or fireplace this time of year.
Frick Pond Loop. Photo by Jessie Li.
Willowemoc Wild Forest. Photo by Alexa Suess.
roxbury, delaware county
Kirkside Park.
Jay Gould Memorial Church.
Roxbury is the birthplace of two wildly different 19th-century notables who began as farm boys and classmates: railroad baron Jay Gould (b. 1836) and naturalist John Burroughs (b. 1837). Gould grew up on a hardscrabble dairy farm, loathed the work, and left as soon as he could to seek his fortune; Burroughs credited those early years with inspiring his passion for nature and philosophy. Both left their marks on Roxbury: Gould in the form of a handsome Reform church with Tiffany stained glass windows, Burroughs with Woodchuck Lodge, his unpretentious and lovely summer residence, now a national historic site.
Today’s Roxbury is layered with elegant creativity. The local motel’s rooms and cottages are fantasy themed, leading Travel and Leisure to call it “the most magical hotel stay in the world.” The Roxbury Arts Center infuses the area with glowing gems of visual and performance art. Kirkside Park is an enchanting spot for a riverside picnic. Book a Table to Farm Tour to get an inside look at Catskills agriculture, or take a hike on Plattekill Mountain (they’ve got glamping too!), or head up to the hamlet of Grand Gorge for true foliage immersion. Whatever you find to do here, don’t forget to pause and look up at the spectacular nighttime sky.
The Roxbury Arts Center.
Woodchuck Lodge.
Plattekill Mountain.
rhinebeck, dutchess county
Rhinebeck was once the violet capital of the world, shipping many thousands of the fragrant purple blooms from both large commercial and small cottage-farm greenhouses. It’s been a prosperous place since its beginnings. People who could afford to live anywhere have often chosen Rhinebeck, and spending some time in this crisp, classic village will give you a feel for their reasons—it drips with prettiness and charm.
Village of Rhinebeck.
It’s also a country village with a big heart, a place where the famous and the farmy still rub elbows to mutual delight. Wander the tree-lined streets, check out the country-chic apparel and the independent jewelers, shop at Hammertown or Montgomery Row, and explore some exquisite jewelry stores. The shopping here is really top notch. Then dine on fabulous farm-to-table food prepared by your choice of expert chefs—Terrapin and Gigi Trattoria are both local favorites
Surrounded by entertainment venues—such as the Dutchess County Fairgrounds, the Old Rhinebeck Aerodrome, and the Fisher Center at Bard College—there’s always a lot going on. You’re also close to Hyde Park, with its historic trea sures and fabulous eats offered by the five Culinary Institute of America restaurants.
Montgomery Row.
Terrapin Restaurant.
Climb Burger Hill at Drayton Grant Park for a stunning panorama of autumn Catskills colors. Wander the tree-lined streets, check out the country-chic apparel and the independent jewelers, browse the exceptional bookstore. Tour the award-winning Omega Center for Sustainable Living, part of the world’s premiere holistic education center.
As autumn settles in, Rhinebeck becomes especially inviting. The air turns brisk, the hillsides around town ignite with color, and the village takes on a quieter rhythm. Locals linger longer at cafés, and weekend visitors stroll the sidewalks with scarves and cider in hand. The farmers market brims with late harvest produce and handmade goods, while the scent of woodsmoke drifts through the side streets. It’s the kind of village that makes you want to linger just a little longer.
Dutchess County Fairgrounds.
Old Rhinebeck Aerodrome.
Fisher Center at Bard College.
Culinary Institute of America.
Burger Hill. Photo by Mike Rokicki.
Omega Center for Sustainable Living.
