4 Day Trip Itineraries to Follow in the Hudson Valley

In the mood for an adventure? Follow these day trip guides for a chance to explore new-to-you corners of the Hudson Valley.

To truly enjoy the natural beauty of the Hudson Valley this spring, hop in your car and hit the road! We’ve mapped out four great excursions in four different counties. Our roundup of top towns includes the best spots to eat, drink, shop, explore, and stay—just in case one day isn’t enough.

Trip 1: Columbia County

Discover the rich history of Columbia: Germantown and Claverack were two of the seven original towns of the county and are full of charm. Their sibling, Hudson, is a vibrant city with so much to do, including top-notch antiquing, dining, and accommodations.

Germantown

SHOP Find your next favorite piece of jewelry at Mary MacGill’s studio on Main Street. Her signature designs of hammered gold and semi-precious stones are simple and striking. A few doors down is Alder & Co., a lifestyle boutique offering everything from on-trend clothing to chic totes, ceramics, and vintage home décor.

EAT AND DRINK Head to Otto’s, a circa-1927 grocer with prepared food, sandwiches, and pastries, or enjoy a farm-to-table meal at Gaskins. For happy hour stop by Tousey Winery, known for its sparkling wines and charcuterie pairings.

PLAY There are spectacular views of the Hudson and northern Catskill Mountains from Ernest R. Lasher Jr. Memorial Park. Clermont Historic Site, once the home of the prominent Livingston family (Robert R. Livingston was a Founding Father), is a perfect spot for birdwatching, walking trails, and strolling through four European-style gardens.

STAY The Central House is a six-suite inn with a grand porch and stunning great room that’s been a Germantown staple since 1876. (It was owned by the Rockefeller family in the early twentieth century.)

Hudson

10 Miles North

SHOP There’s truly something for everyone here: order a beer and peruse best-sellers at Spotty Dog Books & Ale, create a scented candle at Poured Candle Bar, or find a great new piece for your home at Hudson Home, MINNA, Clove & Creek, and LikeMinded Objects. Love antiquing? Head to Antigo, FINCH, and the 40,000-square-foot Antique Warehouse on South Front Street.

EAT AND DRINK The city’s constantly evolving culinary scene means there are many, many great places to eat: Grazin’ takes diner food to the next level thanks to partnerships with nearby farms and Swoon Kitchenbar serves up fresh New England oysters, seasonal mains like slow-braised pork shoulder and house-made pasta, plus a unique selection of wines. Its sister restaurant, Le Perche, is a pretty French bakery and restaurant. Order quality coffee at MOTO, a motorcycle shop that lets you sip cappuccinos while checking out Moto Guzzis and Ducatis.

PLAY Visit the FASNY Museum of Firefighting, the world’s largest museum of its kind. It’s home to old firetrucks (including hose carts from the 1700s) and interactive exhibits for kids. There’s also Hudson Hall, a historic opera house that hosts performances such as the annual Hudson Jazz Festival, and Basilica Hudson, a 19th-century restored factory with live music and art exhibitions.

STAY The Hudson Whaler is a restored three-story hotel with 16 suites and a grandiose lobby inspired by ship interiors; The Maker Hotel is a luxurious getaway with 11 intimate suites, plus an in-house café and glass conservatory-turned-restaurant, a hidden cocktail lounge, and gym with cool, old-school equipment; and Wm. Farmer & Sons features seven charming guest rooms and suites in 19th-century buildings plus a restaurant with an excellent North Carolina-inspired menu.

Claverack

4 Miles East

SHOP Female-owned and family-operated Cooper’s Daughter Spirits is known for its infused vodkas and flavored bourbons. Grab 4-packs of Spookrock NEIPA or Dunbar Stout at the Old Klaverack Hop Farm, a farm brewery. MX Morningstar Farm is ideal for fresh produce, dairy, and more.

EAT AND DRINK Coyote Flaco serves up quesadillas, tacos, and margaritas from their bar or outdoor patio. Local 111 highlights Columbia County’s farms with its inventive American menu. If you’re looking for a no-frills spot, head to Jackson’s BBQ for ribs, burgers, fried fish, and ice cream.

PLAY Brush up on your strokes with a day pass at Columbia Golf & Country Club’s 18-hole course. (There are also tennis and pickleball courts.) Or hike at High Falls Conservation Area, where windy trails lead you to the county’s highest waterfall.

STAY In nearby Craryville, 1805 House Bed & Breakfast is a lovely rural retreat.

Trip 2: Dutchess County

This area is renowned for peaceful, bucolic living along with plenty of culture and fine dining experiences. You’ll be treated to treasures old and new, from antiquing centers and relaxing retreats to a one-of-a-kind drive-in theater, strolling gardens, and a very special high school zoo.

Millbrook

SHOP Upgrade your bath and body products with organic oil infused bars and scrubs from Soaps & Aromatics by Sandra. Explore both the Millbrook Antiques Mall and two-story Antiques Center, which has over 35 dealers.

EAT AND DRINK The bar at Canoe Hill is a draw with $2 oysters and drink specials. Or opt for a stellar sandwich from Babette’s Kitchen or bistro entrees at Café Les Baux.

PLAY Innisfree Garden is a 150-acre, Japanese- and Chinese-style strolling garden with beautiful flora. More adventurous road trippers can shoot sporting clays and go fly fishing at Orvis Sandanona, the oldest shooting preserve in the country. On the outskirts of the village—and a bit closer to Amenia—is the excellent Trevor Zoo on the campus of the Millbrook School with over 170 exotic and indigenous animals.

STAY The Millbrook Inn is full of rural charm and luxe amenities. Don’t miss the on-site farm-to-inn restaurant, The Vintage, which serves up delicious brunch and dinner menus.

Amenia

10 Miles Northeast

SHOP RiverTown Trade, a lifestyle boutique, has a curated collection of artisanal goods, vintage clothing, and repurposed furniture. A few doors down are two small antique shops, Amenia Station and Apple Antiques, that are worth checking out.

EAT AND DRINK Sample Armenian and Iranian cuisine at Serevan, an acclaimed Mediterranean restaurant. (The chef, Serge Madikians, is a James Beard Foundation Award semifinalist.) Four Brothers Pizza Inn and Amenia Steakhouse are long-time favorites. Make sure to leave room for dessert: Fudgy’s Ice Cream offers dozens of unique flavors.

PLAY Four Brothers Drive-In goes beyond movies with an arcade, putt-putt course, pop-ups (like the Grand Bazaar, an annual vendor market, and Good Boys food trucks), and two on-site restaurants. About 10 minutes north, you’ll enjoy Wethersfield Estate & Garden, a Georgian Revival home and Italian Renaissance-inspired garden on over 1,000 acres.

STAY You can spend the night at Four Brothers’ Hotel Caravana, converted airstream vans decked out with kitchenettes (bookings include a double-feature showing). For a more deluxe overnight, head to Troutbeck, a circa-1919 manor that sits on 250 acres of serene farmland.

Millerton

9 Miles North

SHOP Oblong Books is a beloved independent bookseller. Look for staff picks, exclusive editions, and the occasional signed copy. Just around the corner is Oblong Jr. for kid’s picture books, games, and toys. Get your antiquing on at Hunter Bee—a design-forward shop with rustic, industrial, and mid-century pieces—and Millerton Antiques Center, a vast emporium.

EAT AND DRINK The town is home to the headquarters of tea and coffee companies Harney & Sons and Irving Farm—both of which have café menus of fresh soups, sandwiches, and salads. Between Amenia and Millerton, award-winning cidery Kings Highway pours glasses of dry, hard cider made with HV apples and no added sugar; popular flavors include Guavalicious (fermented guava) and the Ginger Snap (roasted ginger and lemongrass).

PLAY The 26-mile Harlem Valley Rail Trail has an entrance right on Main Street. The trail winds through Amenia and Millerton and is open to hikers and cyclists.

STAY The circa-1860s Millerton Inn is a recently renovated elegant Victorian with a Mediterranean restaurant and tap room.

Trip 3: Greene County

Hugging the western shore of the Hudson River, these petite historic towns are growing fast—and for good reason. Home to one of the region’s most prominent artistic movements, Catskill has always been a cultural hub. And its northern neighbors are swiftly following suit.

Catskill

SHOP It’s all happening on Main Street. Kaaterskill Market sells locally made sustainable items for the home. At Citiot, you’ll find fun books, pantry staples, ceramics, and the occasional vintage find. Round out your shopping trip with stops at Magpie Bookshop, Catskill Chocolate Co., and Fisheye Ceramics.

EAT AND DRINK Stop for brunch at the Asian-Latin Mermaid Cafe (we recommend any of the baked empanadas), Willa’s (the babka French toast is outstanding), or New York Restaurant (the Polish-inspired menu includes great pierogis). Subversive Malting + Brewing is a farmhouse brewery that serves up excellent craft beers along with smash burgers, grilled cheese sandwiches, and French fries.

PLAY Bird lovers will enjoy the RamsHorn-Livingston Audubon Sanctuary, a 436-acre preserve that you can stroll or kayak while viewing loons, wood ducks, and great blue herons. Also worth visiting: The Thomas Cole National Historic Site and the Hudson River Skywalk, a 6-mile-long pedestrian walkway that connects the museum with Frederic Church’s home, Olana, in Hudson, and has sweeping views of the Catskills.

STAY About 15 minutes from Main Street, secluded Piaule is super cool. The self-described “landscape hotel” has over a dozen modern cabins with floor-to-ceiling windows and breathtaking mountain views.

Athens

5 Miles North

SHOP Athens Antiques specializes in mid-century pottery, among other timeless finds. Fashion boutique Athens Studio sells vintage and modern clothing and accessories. Lighthouse Liquors and Wines stocks over 700 wines.

EAT AND DRINK Locals rave about Stella’s Pizzeria. Crossroads Brewing, housed in the historic Brooks Opera House, has 10 beers on tap and excellent fried chicken sandwiches. Stop for coffee at The Athens Rooster, which also serves breakfast burritos, over a dozen sandwiches, and brunch pizza (with baked eggs and sausage over crispy dough) on weekends.

PLAY Bring your kayak (or rent one from Screaming Eagle Outdoor Adventures, which also offers guided tours) and head to the Athens Kayak Launch to paddle on the Hudson and sightsee the Middle Ground Flats (an island between Athens and Hudson) and the 1873 Hudson Athens Lighthouse.

STAY The Stewart House dates to 1883 and is currently a nine-room upscale hotel with an art deco restaurant serving American cuisine, an outdoor bistro right on the river, and live music on weekends.

Coxsackie

6 Miles North

SHOP For an eclectic collection of antiques and quirky finds, check out UnQuiet Upstate. Steve’s Clothes and The Babe Cave have a cool mix of vintage and mended apparel. Mansion + Reed is a general store with an espresso bar, baked goods, and locally sourced groceries. The Reed Street Bottle Shop is a great place to stock up your bar cart with canned cider and apéritifs, wine, and spirits.

EAT AND DRINK The Yellow Deli’s bread is house made and the sandwiches, served with coleslaw or chips, are delicious. There’s also Cask & Rasher, a gastropub with killer barbecue and Roman-style pizza, and Italian bistro Che Figata.

PLAY After strolling through the town’s quaint Riverside Park, get back in your kayak and explore the shores of Rattlesnake and Coxsackie islands, two of the seven uninhabited islands between Columbia and Greene counties.

STAY Fifteen minutes southwest, Gather Greene offers a prime glamping experience—ideal for nature lovers who want a bit of luxury. Their 17 treehouse-like cedar cabins feature floor-to-ceiling windows for glorious views.

Trip 4: Sullivan County

The Borscht Belt has been reinvented—and it’s better than ever, thanks to an influx of transplants investing in the area. While the food and shopping scenes have gotten makeovers, there’s a ton of nostalgia—like fly fishing, vintage architecture, and quaint accommodations—to enjoy.

Livingston Manor

SHOP Modern general store DROOZ and Company has thoughtful gifts for kids, candles and reed diffusers, embroidered pillows, and pantry goods. Long Weekend is a vintage Seventies design studio with furnishings, arc lamps, and hand-knotted rugs. Concrete + Water sells on-trend accessories and jewelry for both women and men.

EAT AND DRINK Did you know a craft beverage trail winds through Livingston Manor and other Sullivan towns? Visit New York Brewers’ Association winners Upward Brewing, which is situated on a 120-acre preserve, and Catskill Brewery, whose fan-favorite IPAs (plus other craft beers) are made with Catskill mountain water. Other spots worth visiting: The Kaatskeller, a wood-fired pizza haven with a big outdoor patio; Sunshine Colony, a hip and homey wine bar; Main Street Farm, a café with local goods; and Little North, a market that specializes in rotisserie chicken.

PLAY The area is the birthplace of fly fishing. (Livingston Manor is also home to the Catskill Flyfishing Center & Museum.) Gear up at Dette Flies, a staple for rods, reels, and tackle since 1928.

STAY Along the Willowemoc Creek is The DeBruce, a retreat with clawfoot tubs, cozy sitting areas, and a farm-to-table restaurant. Its sister hotel, The Arnold House, is south of town at the base of Shandelee Mountain and just as charming. Both offer fly fishing, yoga classes, and access to private hiking trails.

Callicoon

19 Miles Southwest

SHOP Stroll down Lower Main to Spruce Home Goods, a petite shop with imported pantry goods, cheese, and excellent coffee in the front and a well-edited selection of rugs, kitchenware, and home accessories in the rear. The Callicoon Pantry and Litt Home + Book offer vintage finds, bulk items, eccentric reads, wellness products, and more.

EAT AND DRINK Locals say Callicoon Wine Merchant has some of the “best tapas in Sullivan.” It also has a curated selection of organic wine and beer on tap and a quaint outdoor seating area. Peppino’s and Local Pizza are the spots for Italian along the river. The Kitchen Table Cafe serves up sandwiches, pastries, and coffee. And the big black building on Upper Main, home to Catskill Provisions Distillery, always draws a crowd—both for their award-winning spirits and the charcuterie and bistro menu available on weekends.

PLAY Catch a movie at the Callicoon Theater, the oldest continuously operating cinema in the county. If it’s too nice to be indoors, book a canoe or kayak excursion with Lander’s River Trips, beginning in May. (You can also rent rafts from their Narrowsburg base.)

STAY Seminary Hill Catskills is a cidery and hotel (along Route 97) with stunning views of the Delaware. The Western Hotel on Upper Main dates to the 1850s and features 10 bright and spacious guestrooms.

Narrowsburg

14 Miles South

SHOP One Grand Books highlights reads hand-picked by celebs and public figures. MayerWasner is an eclectic clothing boutique with indie designers. The Velvet Maple offers vintage and high-end pieces for the home. Sunny’s Pop (owned by Sunrise Ruffalo, wife of actor Mark Ruffalo) sells locally made goods and chic homewares.

EAT AND DRINK Upscale and intimate, The Heron cooks up New American. The Laundrette does pizza and salad right and has a lovely porch overlooking the Delaware. Grab something for the road at Proper to Go, a specialty grocer.

PLAY Take an overhead peek of Narrowsburg and the Delaware River from the summit of Mount Tusten. The 2.9-mile Tusten Mountain Trail loop has several river and quarry lookouts. Check out Tusten Theatre’s upcoming calendar for a range of performances, plays, film showings, and exhibitions from the local community.

STAY The Blue Fox Motel, born in the ‘50s and revamped in 2019, has cozy rooms, cabins, and guest houses—plus casual dining, a pool, and on-site activities.