Nestled in a lushly forested stretch of southwest Ulster County at the foot of the Shawangunk Ridge, Ellenville is a quiet mountain village of 4,100 whose 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. Here’s a two-day guide to exploring the hidden delights of Ellenville.

Day 1

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 at Wilson’s Market on Canal or a quick cup of Joe at B&B Coffee Shop on Main Street.

Cohen's Bakery in Ellenville, NY

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.

After a morning of high-impact physical activity, cool off with a local brew and German-influenced bite from New Paltz 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.

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.

For dinner, treat yourself to one of Ellenville’s upscale eateries along Canal Street. Trattoria Marbella is a white tablecloth Italian spot serving fresh Tuscan-inspired cuisine Pasta con Tuna and Risotto Primavera. 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. Their 2019 season line-up includes the chamber drama “The Roommate” by award-winning playwright Jen Silverman and the salon-set comedy-mystery “Shear Madness” by Paul Porter.

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

Day 2

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

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.

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.)

Sook House in Ellenville, NY

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.

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.

Ready for an Ellenville adventure? Start planning your trip today.