Nestled in a lushly forested stretch of southwest Ulster County at the foot of the Shawangunk Ridge, Ellenville is a quiet mountain village in Wawarsing, NY. This town’s laidback rural spirit belies a sophisticated dining scene and one of the most acclaimed professional theatre companies in the Hudson Valley, in addition to the outdoor recreation and scenic beauty the area is known for. 

If you’re looking for a scenic and relaxing weekend, here’s a two-day guide to exploring the hidden delights of things to do in Ellenville, NY.

Day 1: Famous Trails, Historic Museums, and the Theater

Pick Up Coffee and a Pastry to Kick Off the Weekend

Start your morning with a coffee and pastry from the famous Cohen’s Bakery on Center Street, a staple of downtown for nearly 100 years. The company’s founder, the late Harry Cohen, is the purported inventor of raisin pumpernickel bread, and his original recipe is still used at the bakery to this day. You can also grab a breakfast sandwich, pastries, an excellent cup of coffee, and all sorts of other amazing things at Morning Sunshine on the corner of Center St and Clinton Avenue.

Cohen's Bakery in Ellenville, NY

Explore the Local Trails

Once you’ve had your morning coffee, grab your mountain bike and drive north on 209 a few miles to Lippman Park, then spend the morning exploring the winding, elevated paths of the 14-mile Lippman Park Mountain Bike Trail. This famous trail system is known for its raised boardwalks, bridges, and berms, and it can get quite challenging as you ascend the mountain. (Novice tip: for an easier time stick the trails near the base of the mountain). 

If mountain biking isn’t your thing, consider an adventure tour of the surrounding forest and mountains with Northeast Off-Road Adventures, which also offers off-road driving lessons, as well as wilderness survival skills and first aid classes.

Grab Lunch and a Cold One

After a morning of high-impact physical activity, cool off with a house-made beer and enjoy a menu of inventive American bites from Rough Cut Brewing Co. Or, for a full sit-down lunch, head back to Ellenville and grab a sandwich, salad or wrap from The Publik House or chow down on BBQ from Smoken Mos.

Take in a Museum

After lunch, pop into the Ellenville Public Library’s Terwilliger House Museum on Center Street, a late 19th Century Queen Anne Victorian House built in 1895 and today houses a fascinating collection of local historical artifacts. Spend the rest of the afternoon window shopping and exploring the quaint charm of Ellenville’s Downtown Historic District.

End Your Day with Dinner and a Show

For dinner, try Marbella, a Tapa wine bar with exceptional contemporary American plates made with Italian and French influences. Down the street, Tony & Nick’s Italian Kitchen pulls double duty as a family-run classic Italian joint that’s also one of the best spots in town for live music.

After dinner, catch a show at Shadowland Stages, regarded as one of the best New York playhouses north of the City. Featuring the talents of some of New York’s most exciting actors, directors, and comics you can find their latest shows here.

Cap your evening with post-show cocktails at one of a handful of late-night spots in walking distance.

Day 2: Outdoor Adventure, Eclectic Meals, and Wine Tours

Fly High to Get Your Day Started

Start your second day with a high-flying adventure. Mountain Wings offers thrilling hang-gliding trips for both experienced hang-gliders and first-timers, giving you a gorgeous bird’s eye view of the mid-Hudson Valley.

Hang gliding in Ellenville, NY

Enjoy Diverse and Delicious Lunch Options

For lunch, grab a gourmet pizza from Arianna’s Restaurant & Pizzeria on Market or a New York slice from Dominick’s on Center Street. If you’re not feeling pizza, step into the aromatic wonderland of Island Pepper Pot & Lounge on Liberty Street (serving delicious Caribbean fare like jerk chicken and oxtail soup) or try the sushi at Sook House on Center Street, which also serves Korean fare like dumplings and bibimbap. If you’re looking for a quick takeout bite, New China One has you covered.

Sook House in Ellenville, NY

Wind Down With a Wine Tour

After lunch, hop on Highway 52 heading west and take a drive down the gorgeous Shawangunk Mountains Scenic Byway. From there, you’ll find yourself on a stretch of the 80-mile Shawangunk Wine Trail. Stop by Brimstone Hill Vineyard for a tasting, then grab a glass from Baldwin Vineyards. From there, you can keep going west and hit several more wineries, or you can double back to Ellenville in preparation for another stellar dinner. (Just remember: have a designated driver and don’t drink before you get behind the wheel.)

If you prefer fresh fruit to fermented, skip the wine trail and head to Barthel’s Farm Market on Rt. 209, where you’ll find freshly harvested fruits and vegetables, homemade baked goods and apple cider, and locally made ice cream.

Finish Your Weekend with Another Amazing Meal and One Last Wine Stop

For dinner, you have several amazing options besides the ones already mentioned. The Green-certified Aroma Thyme Bistro on Canal Street has cultivated a national reputation as one of the most beloved farm-to-table restaurants in the country, thanks to the uncompromising ethos and innovative seasonal menus of co-owners Jamie and Chef Marcus Guiliano. If you’re in the mood for Mexican, Gaby’s Café, also on Canal, features a sprawling menu of traditional Mexican fare (along with killer margaritas) in a classy casual space.

End your day with one last wine stop by heading to Sideways, an adorable outdoor wine bar located in the center of the village off Liberty Square. Owned and operated by a Georgian wine connoisseur, the selection is fabulous and the sunsets are amazing.

Get Ready for a Weekend in Ellenville, NY

Spending a weekend in Ellenville offers a perfect blend of scenic beauty, outdoor adventure, and culinary delights. Whether you’re biking the trails, exploring local museums, savoring gourmet meals, or catching a show, Ellenville provides a memorable experience for all visitors. 

Ready for an Ellenville, NY adventure? Start planning your trip today!