By Francesca Furey and Megan Wilson
Why We Love It
This recently revamped (and nearly century-old) guest house is an art lover’s paradise. Located in the heart of Woodstock, a town with plenty of bohemian draw itself, Twin Gables is part bunkhouse, part hotel. All 10 rooms are unique—“room 6” is a single with a striking deep-green painted ceiling inspired by nearby Hunter Mountain; “room 11” features a king bed and whimsical wall stencils. There’s also plenty of hand-painted murals and decorative items throughout the hallways and communal parlor. We appreciated the locally-sourced continental breakfast of fruits and pastries and 24/7 tea and coffee bar in the kitchen. But our favorite amenities at this “little art hotel” are the secret garden—a secluded outdoor seating area away from the bustle of Tinker Street; the private gazebo with its rainbow-painted ceiling; and the backyard fire pit. The Twin Gables’ finished attic space serves as a communal studio where you can work, meditate, or BYO art supplies and just get creative.
Start your morning with an energizing two-days-steeped nitro brew and wood-fired bagels while listening to indie music at The Mud Club (themudclub.com). Stop by Friday–Sunday after 5 p.m. for their seriously delicious sourdough pizzas.
The Mud Club’s sister location, Early Terrible (earlyterrible.com), is a tapas bar serving up specialties like Armenian chicken kebabs and grilled chorizo with avo chickpea salad, plus cocktails that pack a punch.
Chances are you’ve heard of Hudson Valley’s favorite local bakery chain: Bread Alone (breadalone.com). Grab a loaf or baguette to go, or order the smoked salmon sandwich, stacked high with cream cheese, cucumbers, and dill.
Indulge in Route 66-style comfort food at Dixon Roadside (dixonroadside.com). We highly recommend the mac and cheese, especially paired with lime salt steak fries and fluffy buttermilk biscuits. Oh, and their fried chicken is unreal.
Why We Love It
Simple and chic, this 20-room hotel features fresh takes on the classic Catskills getaway, emphasizing solitude and coziness. Graham & Co. calls its accommodations (several of which are dog-friendly) “unpretentious but considered,” and provides a comfortable, peaceful escape. The décor is neutral and natural with woodsy adornments like mounted faux antlers and animal hide rugs. Choose from six different room styles, ranging from a homey standard single with a queen bed to a secluded two-bedroom bungalow with a kitchenette and a living room. Less than half a mile from Phoenicia’s Main Street, Graham & Co. offers free-to-use bikes for guests to explore the area. At night, unwind around the bonfire or catch a movie in the den, a hip white-brick room with a large sectional and old-school games.
Treat yourself to the Full Phoenicia Breakfast or savory avocado street corn toast at the famed Phoenicia Diner (phoeniciadiner.com). Enjoy your meal inside the retro airstream, or at picnic tables covered by a wooden pavilion.
Visit the Catskills Division of Rail Explorers (railexplorers.net) and immerse yourself in the stunning scenery of the Esopus Creek. With no cell service, the tour requires you to fully unplug while peddling through the 8-mile round trip on your group’s railroad cart.
A downtown mainstay, Brio’s (brios.net) is beloved for their thin-crust Neapolitan-style pizza. Go for the margherita—let’s face it, it never gets old—or branch out and order the wild mushroom, made with a sesame seed crust and drizzled with truffle oil.
Grab a pint or two at Woodstock Brewing (drinkwoodstock.com), which offers up 15 craft beers on tap, including the highly recommended Baby Dragon, their flagship pale ale. Order a few small plates, like their insanely addicting beer-battered onion rings, and buy a four-pack on your way out.
Why We Love It
At the intersection of mid-century modern and minimalist design, you’ll find Eastwind. A unique getaway with Scandinavian sensibilities, the hotel offers 26 accommodations (many of which are pet-friendly), ranging from the Writer Studio with one king bed and the ADA-accessible Hill House King to the highly-Instagrammable Lushna suites for a self-described “almost-camping” experience. The suites’ natural wood ushers in a plethora of light and the spaces feature welcoming accents like Turkish rugs and succulent plants. We especially appreciated the hotel’s sauna and bar, which offers up small plates and seasonal cocktails, available to guests until 9 p.m. nightly for room service, and Friday–Saturday for indoor dining by reservation.
Start your morning with a hearty country breakfast from Catskill Mountain Country Store & Restaurant (catskillmtncountrystore.com). Go for a specialty omelet like the Tall Tale, made with smoked salmon, sour cream, and chives, or dig into a pancake platter.
Windham Fine Arts (windhamfinearts.com) is a contemporary gallery with plenty of Catskills charm (it’s in a renovated 1855 home) in the heart of historic downtown. There’s over 3,000 sq-ft of work, like synergistic pieces, realistic landscapes, and regional scenes.
Are we in the French countryside or the Catskills? At Bistro Brie & Bordeaux (bistrobrieandbordeaux.com), you’ll find yourself lost in its ambiance of French jazz music, fine art, and flowers on every table, while enjoying escargot and French onion soup.
Ski the slopes and tube down the trails of Windham Mountain (windhammountain.com), a one-stop destination for outdoor fun. For something a bit more lowkey, check out the ice rink at its base.
Why We Love It
Tucked at the tail end of bustling Tinker Street is this delightfully quirky inn. Four distinct and private flats—named after music icons Carole King, Aretha Franklin, Stevie Nicks, and Joni Mitchell—are prepped with kitchenettes and pretty bathrooms perfect for those who want an extended stay in Woodstock. The inn is designed with funky wallpaper, vinyl records, board games, and statement pieces you wish you had in your own home. There’s even a red cedar hot tub in the backyard. Adam Wolbarst and Carmen Rodriguez, owners and newlyweds, created this fun spot to be completely self-serviced— check-in comes in the form of an email with a code. Stickers are smartly placed throughout your room, detailing WiFi info and appliance instructions, and each suite comes with an iPad to help you research Woodstock’s dining and shopping scene. Furry friends are welcome in Mitchell Manor and Franklin Flat, both ground-floor suites with access to private patios. Check out The Commune to mingle with other guests and buy local goods, like scents from aromatherapy brand Root and Resin (their signature Herwood scent is diffused in your flat, BTW). There are also free-to-use bikes and sleds available for guests.
Come for the 52-year-old drip candle mountain (seriously, it’s over 6 feet tall) and stay for the vast selection of candles, waxes, and home décor at Candlestock (candlestock.com). We’re especially fond of their candle mushrooms and funky tie dye veneer candles. Right down the road, you’ll find eco-friendly items like fun greeting cards embedded with seeds (plant the cards in soil, and they’ll grow!), toothpowder, and bath salts at Lovewild Design (lovewilddesign.com).
Trek the trails of Overlook Mountain, the southernmost peak of the Catskill Escarpment. While passing through, hike around the ruins of the Overlook Mountain Hotel, a historic late 19th-century resort. If elevation isn’t your thing, take a quick drive to the Ashokan Rail Trail for flat, picturesque hike and bike trails along the reservoir.
In the mood for live music? Head over to Colony (colonywoodstock.com) where you can hang out in the beer garden or catch a show in the restored 1929 ballroom-style theater. Or check the events calendar at the famous Bearsville Theater (bearsvilletheater.com) where Peter, Paul and Mary, and Bob Dylan performed in the ‘60s.