Hudson Valley Wine Trail Itinerary: Best Wineries & Hotels

By | Wine Writer & Wine Judge
Last Updated: September 18, 2023
Hudson Valley Wine Trail Itinerary: Best Wineries & Hotels • Winetraveler

The Hudson Valley has been an area for New York City dwellers to shake off some city living for eons. These days with domestic travel being so hot, it’s become a popular destination for travelers all over. The Hudson Valley wine region is becoming more well-known around the world as well and has made the region even more en vogue. With the wineries interspersed between the rolling hills of farmland and impressive mountains, it can be daunting to find a place to stay with easy wine trail access but we have made it simple.

RELATED: Hudson Valley & Catskill Mountains Road Trip Itinerary

The Shawangunk Wine Trail is home to a number of wineries nestled between the Shawangunk Mountains (locally called The ‘Gunks) and the Hudson River, just 60 miles north of NYC. It’s a stunning region to explore by car, so consider renting a car if you’d like the room to roam. All of the wineries on the trail are easy enough to visit from one central location.

Hudson Valley Wine Tours

A great way to visit Hudson Valley wineries without worrying about driving is to book a 2-day winery and hiking experience, operated by Active Lifestyle Tours. Single-day tour options are also available. This adventure allows you to explore Nostrano Vineyards and Benmarl Vineyards and Winery and more. Immerse yourself in nature with a hike in Beacon and a leisurely walk across the Walkway Over the Hudson. Enjoy ample free time to discover the charming city of Beacon, New York. Your overnight stay and breakfast on the second day are all taken care of, ensuring a stress-free and memorable experience.

If you’d like to discover some of the amazing craft beer in the region, another fun options is take a craft beer and bike tour through the scenic Hudson Valley, operated by Gotham Bicycle Tours.

One other unique option in the region is to take a private helicopter tour! On this experience, you’re even allowed to take the controls yourself.

The Hudson Valley is also known for its incredible farms and food. Take a local alpaca hike and farm tour, a great option if you’re traveling with kids.

Hudson Valley Wine Trail Itinerary: Best Wineries & Hotels • Winetraveler
Beautiful view looking out over the Hudson Valley at sunset.

The Hudson Valley wine region is known for quaint historic inns, mountain houses, and serene spas. We have broken up the trail into three parts to easily choose a centralized location to the wineries you want to hit.

Best Hudson Valley Wineries & Hotels


Where to Stay

Beekman Arms & Delamater Inn

This inn has welcomed guests to the beauty of the Hudson Valley since before the Revolutionary War. The property has operated continuously since 1766, retaining much of its colonial charm and character. Enjoy great food and a drink at the bar or in the garden. The thick wooden doors, wide planked floors, and stone fireplaces provide a great historical atmosphere.

Buttermilk Falls Inn & Spa

Located in Milton, Buttermilk is a sprawling 75-acre estate that offers a remarkable selection of lodgings, a world-class spa, a farm-to-table restaurant, an organic kitchen garden and orchard, trails and an animal rescue sanctuary.

Danskammer House

This house began as a handsome 1870 private residence in colonial revival style and was later transformed into the medical clinic and residence of the village doctor, J.B. Scott, after the Second World War. Today, Danskammer House offers bed-and-breakfast style accommodations in five private guest room suites. Guests can take advantage of the panoramic third-floor lounge, first-floor living room, dining room, and garden room, as well as outdoor areas strewn with orchards, berry patches, and gardens.

Saint Hubert Lodge & Club

The Saint Hubert Lodge & Club in Marlboro is a number of modern rustic inns in one. The main spot is the lodge which features three suites, a jacuzzi, an outdoor fireplace and a pool. There are also separate inns such as The Caretaker’s Quarters, Rustic Log Cabin, or the Kennel Cabin that are tucked away in the woods.

Upper East Gunks Hudson Valley Wineries

Benmarl Winery

156 Highland Ave, Marlboro, NY 12542

(845) 236-4265

Benmarl winery in Marlboro is the oldest vineyard in America. They are known for their Hudson River Valley grown Cabernet Franc (the region’s signature grape!) and their Rieslings. Choose from outdoor tastings on the farm surrounded by the mountains or inside the taproom. 

Fjord Vineyards

251 Ridge Rd, Milton, NY 12547

(845) 393-0094

Fjord Vineyards is owned by the same family and has the same winemaker as Benmarl. It’s right around the corner so it’s an easy twofer. Their Albariño is a show-stopper. The outdoor tasting room is speckled with seating and picnic areas.

Stoutridge Winery & Distillery

10 Ann Kaley Ln, Marlboro, NY 12542

(845) 236-7620

Stoutridge Winery & Distillery in Marlboro is located in an 1800s farmhouse nestled into the side of a limestone ridge. Guided tastings of their spirits and wines are available Thursdays-Sundays and casual enjoyment can be had outdoors overlooking the vineyard and the lovely grounds with pond, waterfall & picnic tables. Food trucks are on-site during busier times.

Glorie Farm Winery

40 Mountain Rd, Marlboro, NY 12542

(845) 236-3265

This is the place to go for an outdoor tasting, apple picking, and live music. Gourmet lite nites are available and pair perfectly with their organic wines. Your dog is welcome to enjoy the views there as well.

RELATED: The Best Wineries to Visit in the Finger Lakes This Year


Where to Stay

The Borland House Inn & Restaurant

The Borland House in Montgomery is a historic inn with 10-foot-ceilings, hand-carved moldings, an artist’s wing, saloon, drawing room, a front porch sitting area, and a farm garden, all with an atmosphere that whispers of a more artful and whimsical time. Each of the rooms is made to be a different bird habitat inspired by the paintings of John James Audubon. Travelers and locals meet daily for afternoon tea in the hall, and at 5 o’clock cocktails are served in the drawing-room. Yancey Migliore, owner of Whitecliff Winery recommends it to her guests. “I absolutely recommend the Borland house,” she says. “Its location is convenient for visiting our wineries, it is beautiful and incredibly historic.”

Audrey’s Farmhouse

Audrey’s Farmhouse is a cedar-shingled farmhouse originally built in 1740, is a 5 bedroom guest house that sleeps 10 and has a full kitchen, 2 living rooms, a wood fireplace,  5 bedrooms, 4 baths including a claw foot tub, a fire pit, and a massive backyard. They also offer The Greenhouse Guestrooms which have private outdoor patios and exterior front doors that open into the Garden Courtyard. Todd Cavallo, owner of Wild Arc praised Audrey’s, saying, “Any of the Audrey’s Farmhouse properties are amazing! It is so beautiful and right at the foot of the ridge with amazing views and access to wineries. The owners Doug and Sally are also great and super nice.”

Brookfield Farm B&B

Brookfield Farm in Modena is a 20-acre country retreat that includes a walking trail, gardens, and swimming pool. It is also home to a few Scottish Highland cows and serves as a wildlife habitat.

Mohonk Mountain House

Mohonk Mountain House sounds small and rustic but is actually an impressive, cliffside Victorian castle that operates as a luxury resort and spa. It is surrounded by 40,000 acres of forest where hiking, kayaking and rock climbing are available. Entertainment and activities know no bounds here and the cuisine is top-notch. Michael Dorf, owner of City Winery, told us he recommends it to guess when his accommodations are booked, saying, “My favorite place in the gunks is the Mohonk—to be able to add some hiking and biking in order to burn off all the calories drank on the trail.”

Best Hudson Valley Hotels in Wine Country Itinerary: Best Wineries & Hotels • Winetraveler
The Mohonk Mountain House in the Upper West Gunks of the Hudson Valley. It’s a cliffside Victorian castle that operates as a luxury resort and spa. Surrounded by 40,000 acres of forest where hiking, kayaking, and rock climbing.
Stage Coach Inn

The Stage Coach Inn in Goshen, built-in 1747, is an old stagecoach stop that’s been fully renovated into a five-star inn and tavern. Rooms are equipped with cozy fireplaces perfect to sip wine by.

Upper West Gunks Hudson Valley Wineries

Whitecliff Winery

331 Mckinstry Rd, Gardiner, NY 12525

(845) 255-4613

Whitecliff Winery in Gardiner is an award-winning winery that has been in business for 30 years. Enveloped by the Shawangunk Mountains, it boasts an impressive spot to taste. Snacks and light bites are offered and dogs are welcome outside.

Robibero Winery

714 Albany Post Rd, New Paltz, NY 12561

(845) 255-9463

Robibero Winery in New Paltz offers live music every weekend and a number of food options, including their wood-fired pizzas. Lawn games and fire pits make it a great spot to hunker down for a bit. 

Wild Arc Farms

918 Hill Ave, Pine Bush, NY 12566

(845) 419-3504

Wild Arc Farms in Pine Bush is a natural and sustainable farm and winery. While they don’t have a taproom or tasting area yet, they are working on a farm stand. Their wines are highly allocated, so it’s a great opportunity to pick some up while visiting the area.

City Winery HV

23 Factory St, Montgomery, NY 12549

(845) 424-0222

City Winery HV is the first City Winery that is not actually in a city! This massive event space and winery is the brainchild of former Knitting Factory NYC owner, Michael Dorf. Big-name acts come through because of his long ties in the music industry. They are working on accommodations on-site. “We are about 18 months from opening our 13-room hotel on the grounds,” says Dorf. “Meanwhile, we have a beautifully restored barn with 3 full suites, including one bridal suite.” 

Christopher Jacobs Pennings Vineyards

320 Crawford St, Pine Bush, NY 12566

(845) 728-8066

Christopher Jacobs Pennings Vineyards is a beautiful spot to take in a sunset and some live music during their Summer Sunset nights. Overlooking the mountains, orchards and winery, the team serves up their line of ciders and wine, along with bites from rotating food trucks.

RELATED: How To Spend a Long Weekend in The Finger Lakes

Best Hudson Valley Wineries and Hotels
The Hudson Valley wine region makes for the perfect road trip escape with its idyllic mountain and wooded scenery.


Where to Stay

Caldwell House B&B

Caldwell House in the Salisbury Mills region of Cornwall is a charming inn that exudes Irish hospitality. Each room includes a jacuzzi and a fireplace and a three-course breakfast is offered each morning. Bonus—not only is this close to the wine trail, but it’s also within walking distance to Jone’s Farm & Shops where you can pick up fresh produce, baked goods and gifts after you feed and pet the animals.

The Dutchess Inn & Spa

The Dutchess in Beacon is a European-style hotel with panoramic views of the Hudson Valley and a fire-side lounge overlooking Main Street. Juan Sanchez, retail manager at Brotherhood, recommends it to visitors, saying, “It’s an upscale inn within walking distance to tons of art galleries, hand-blown glass, restaurants and breweries.”

Fox & Bear Lodge

Fox & Bear in Glenwood, NY is an 1831 colonial mansion featuring wrap-around porches and stunning views. All stays include a continental breakfast and additional goodies like yoga on the greens. Dog-friendly! 

Inn at Stony Creek

Inn at Stony Creek in Warwick is a restored colonial farmhouse built in 1840. Set upon 90 acres, guests can take advantage of walking trails and enjoy the company of the resident ducks and geese.

Chateau Hathorn

Chateau Hathorn in Warwick was once an early American homestead turned authentically furnished 18th-century private mansion. Gorgeous manicured grounds and fine Swiss and French cuisine are just a few things guests can expect.

RELATED: How To Spend a Long Weekend in Aurora, NY

Lower Gunks Hudson Valley Wineries

Brotherhood Winery

100 Brotherhood Plaza Dr, Washingtonville, NY 10992

(845) 496-3661

Brotherhood Winery is the oldest continually operating winery in America. The grounds and tasting room are both equally epic in size and stature. Brotherhood also has two restaurants on-site.

Clearview Winery

35 Clearview Ln, Warwick, NY 10990

(845) 651-2838

Clearview Winery in Warwick is aptly named for its stunning views of the valley. It was once named in Travel+Leisure magazine as a Top U.S. Vineyard. Snacks and live music are available inside the taproom and on the patio outside.

Applewood Winery

82 4 Corners Rd, Warwick, NY 10990

(845) 988-9292

Applewood Winery offers a scenic setting, apple picking, live music and food. For fans of sweeter wines, check out their pink Moscato.

Warwick Valley Winery

114 Little York Rd, Warwick, NY 10990

(845) 258-4858

Warwick Valley Winery is a massive spot to enjoy wine, cider and delicious food. They are known for their music festivals—Dylan Fest being a huge yearly draw. Most of the year, bands play outdoors on the bluestone patios surrounded by rose gardens.  In colder months, musicians play inside while guests warm by the fire.

Have fun on the ‘Gunks!

Frequently Asked Questions about Hudson Valley Wineries

If you enjoyed this guide, consider joining the Winetraveler Facebook Group to connect with other Winetravelers and for additional travel inspiration around the world. Be sure to also follow us on Twitter and Instagram. We also highly recommend taking a look at this itinerary for exploring the Hudson Valley if you’re looking for additional activities outside of visiting wineries.

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