So, hop in the car and head to a place you’ve never been (or haven’t visited in a while). The pretty drive upstate is part of the fun.
Woodstock • Millerton • Hudson • Beacon
Woodstock
Why It’s Great
Though it’s not the original location of the 1969 festival, this vibrant Ulster town has a fantastic music scene with roots in folk and rock: Bearsville Theater was originally a community for legends like Bob Dylan, Janis Joplin, and The Band. Today it has nighttime performances in a renovated theater—but during the day you can tour the grounds to learn about legendary manager Albert Grossman and Bearsville Studios or relax in Bearsville Park (which has picnic tables for snacking and outdoor live music). You can also book a walking tour co-hosted by Rock Junket Tours. For over two hours, you’ll hear fascinating stories, see rare photography and album art, and view old hangout spots of Dylan, Jimi Hendrix, and other rock legends. Bearsville also hosts Sunday jazz shows. Starting in the spring, Colony—an intimate circa-1929 space on Rock City Road—opens its outdoor beer garden for live music (from bluegrass groups to solo indie artists) and pub food.
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Check out Casa Ziki for unique, design-forward home décor and gifts and The Golden Notebook for a great selection of reads. Lovewild Design carries sustainable stationery and low-waste bath and body products, and at Candlestock, you’ll find an array of scented and decorative candles, plus hand-dipped drip candles.
You can easily spend an entire day in Woodstock. The charming town has lots of cool shops and restaurants, and great spots to hear live music.
Eat & Drink
If you arrive at brunch time, hit up Moonrise Bagels—the bagel sandwiches are some of the best around. Grab a heartier bite at Yum Yum Noodle Bar, Sharkie’s (great meatball heroes), or Tinker Taco. Enjoy happy hour at Small Talk. This cocktail bar on Tinker Street, decorated with vintage postcards of the Catskills, mixes up well-executed classics and specialty drinks like the Naked and Famous, made with mezcal, Aperol, yellow chartreuse, and lime.
Millerton
Why It’s Great
It’s an ideal area for adventuring with the family. The 26-mile Harlem Valley Rail Trail (you can hike or bike) cuts right through Millerton—the entrance is on Main Street. If you have the stamina trek three miles north on the HVRT to Taconic State Park, where you’ll find more trails and picturesque Rudd Pond where you can go fishing and boating; there’s beachfront swimming starting Memorial Day weekend. You can also take a 20-minute detour to Trevor Zoo in Millbrook—an accredited, student-run zoo with endangered and exotic animals. If the weather turns, catch a flick at The Moviehouse. There are a several showtimes each day including both kid-friendly and award-winning films.
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Downtown is home to Oblong Books and Oblong Jr. Toys and Books, a cute shop with plenty of picture books and middle-grade reads, puzzles, and more. Adults will enjoy wandering around the Millerton Antique Center, which showcases vintage finds—furniture, vinyl, rugs, and more—from over 35 dealers. Westerlind, a fashion boutique, has chic outdoor apparel and gear.
Eat & Drink
Grab lunch at Oakhurst Diner or Four Brothers Pizza Inn. The diner is known for its farm-to-table fare (the chicken lemongrass dumplings are a favorite) in a retro steel space, plus it has outdoor seating. The Pizza Inn is a Valley institution—share a pie or go for pastas, sandwiches, or chicken fingers. Millerton is also home to not one but two big names in the coffee/tea industry: Harney & Sons and Irving Farm, which both offer fresh iced or hot drinks along with food options such as salads, sandwiches, and pastries.
Millerton has something for everyone—shops, eateries, and the Harlem Valley Rail Trail for hiking and biking.
Hudson
Why It’s Great
Once a whaling hub, Hudson is now lined with high-end boutiques, home décor stores, vintage shops, and plenty of restaurants and bars. Most of the businesses are along (or just off) mile-long Warren Street. Hudson is well-known for its abundance of antique shops. A few to stop in: Cooper and Company, A Collector’s Eye, Arenskjold Antiques, Art, and Modern Design, and Red Chair on Warren. You can also spend an entire day browsing the 40,000-square-foot Antique Warehouse on Front Street.
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For quirky greeting cards, notebooks, planners, and other stationery, stop into The Social Type. Botanical apothecary Florent carries a line of natural skincare products and perfumes. A curated mix of furniture, clothing, linens, rugs, and purses await at Lili and Loo. A popular design firm sets up shop at foley & cox HOME, which offers vintage furnishings, custom-designed outdoor furniture and upholstery, and contemporary art. More décor selected by high-end interior designers can be found at Hudson Home and FINCH, which stocks both vintage and modern furniture, plus apparel, art, lighting, and accessories.
The 400 and 500 blocks are probably the busiest sections of Warren Street. If you want to pick up something for your furry friend, head to Love Thy Beast. You can get books, art supplies, and sip a craft beer at The Spotty Dog Books & Ale. Beautiful fabrics are designed in-house and turned into curtains, pillowcases, table runners, and more at Les Indiennes. Fig & Bella and shoe store Intentionally Blank both carry unique wardrobe accessories; and don’t miss Upstate Rug Supply, which offers a wide collection of antique carpets.
Eat & Drink
The small city teems with culinary talent. Cafe Mutton, which has earned two James Beard Award nominations, appeals with buttery crepes, orange muffins, and pork rillettes toast. Go for bold flavors—and an equally vibrant setting—at Lil Deb’s Oasis. The restaurant, which plates up what it calls “tropical comfort food” has also received several James Beard Award noms since 2019. Le Perche is lovely for brunch or lunch (sit outside if it’s a nice day). At Feast & Floret, dig into farm-to-table Italian served in a beautiful, flower-filled space that was formerly a blacksmith shop. Craft cocktails are the star of the show at The Hereafter, which debuted last year. Order a pint at Union Street Brewing Co., which arrived on the local beer scene in 2023 with its roster of IPAs and lagers.
Beacon
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If you love kitchen gadgets and cookware, you’ll find everything you need at Utensil Kitchenware, from steel saucier pans to Stasher bags to bar glasses, and Stella’s Fine Market, for international and unique pantry goods. Hunca Munca’s has a curated selection of whimsical gifts for children of all ages. Find your next favorite piece of jewelry and calming candles, plus greeting cards and paper goods, at Lewis & Pine. If you’re outdoorsy, Mountain Tops Outfitters and the Last Outpost Store carry hiking gear, footwear, apparel, and accessories. Near the Main Street Park, check out Witch Hazel, an eco-friendly apothecary and beauty store. Across the street is Zakka Joy, a colorful hub for kids and adults alike for stationery and pens to imported Japanese toys and goods to trendy home products. Other notable shops: Little King, a stunning home goods store; Raven Rose for botanical and wellness gifts; and Solstad House, a small general store with creative books, Beacon-inspired merch, and more.
Eat & Drink
From authentic British eats at Moreish, to comfort food at Cooper’s, to Nepalese dumplings at Momo Valley, Beacon has it all.
Standout spots include Nilufer’s Home Kitchen, where chef-owner Nilufer Goodson dazzles patrons with her Turkish cuisine; Cooper’s, which serves elevated comfort foods like short-rib grilled cheese, ahi tuna-topped nachos, and pinsas—a pizza-like Roman flatbread. Hudson Valley Food Hall is home to seven eateries—including Five Pennies Creamery and Moreish, which specializes in British staples like bangers and mash. Choices also abound at Melzingah Tap House, where outside-the-box starters like cantaloupe gazpacho give way to tasty mains like crispy-skin chicken breast and potato dumplings. Dumplings are also on the menu at Momo Valley; the vegan-friendly Nepalese standout excels in its namesake momo dumplings among other Himalayan dishes. At cocktail hour head to Hudson Valley Brewery (best known for their fruit sours), The Vinyl Room (a retro gastropub with good tunes and cocktails), or Happy Valley (bar/arcade).
Why It’s Great
This small city on the Hudson has seen a boom in popularity over the past two decades. Beacon’s past as an industrial hub is still evident on Main Street, but instead of factories, the 19th-century buildings along the mile-long stretch are now chic condos and clothing boutiques, independent art studios, and eclectic eateries. Outdoor destinations like Long Dock Park and Mount Beacon are only minutes away from Main Street, and no trip to Beacon would be complete without a visit to Dia Beacon—one of the largest contemporary art museums in the country.
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