Nick's Guidebook
Food scene
Cozy restaurant with indoor and outdoor dining. Enjoy their large community fire-pit and beautiful grounds. Perfect for a cool fall night! Remember to make a reservation!!
Old Drovers Inn
196 E Duncan Hill RdCozy restaurant with indoor and outdoor dining. Enjoy their large community fire-pit and beautiful grounds. Perfect for a cool fall night! Remember to make a reservation!!
Great Bakery and Restaurant in the heart of the Village of Pawling. Awesome Brunch! Make a reservation!
44 locals recommend
McKinney & Doyle Fine Foods Cafe
10 Charles Colman BlvdGreat Bakery and Restaurant in the heart of the Village of Pawling. Awesome Brunch! Make a reservation!
Our absolute favorite restaurant. Always great food and atmosphere!
58 locals recommend
White Horse Tavern
567 Hudson StreetOur absolute favorite restaurant. Always great food and atmosphere!
Authentic Irish pub. Great place to grab a beer with good friends.
14 locals recommend
O'Connor's Public House
6 Broad StAuthentic Irish pub. Great place to grab a beer with good friends.
Carriage House Restaurant & Tavern
2605 NY-22Hiking
Wonderful short hike around a beautiful lake! Great hike to experience the fall foliage!
9 locals recommend
Nuclear Lake
Wonderful short hike around a beautiful lake! Great hike to experience the fall foliage!
Beautiful hiking and waterfalls! Great for leaf peepers and families!
121 locals recommend
Kent Falls State Park
462 Kent Cornwall RdBeautiful hiking and waterfalls! Great for leaf peepers and families!
The Appalachian Trail runs directly through The Town of Pawling. We are luck enough to have a trailhead just a few miles down the road!
19 locals recommend
Appalachian Trail
3299 Appalachian National Scenic TrailThe Appalachian Trail runs directly through The Town of Pawling. We are luck enough to have a trailhead just a few miles down the road!
Great close hiking just off the Appalachian Trail along the Ten Mile River.
13 locals recommend
Bulls Bridge
Great close hiking just off the Appalachian Trail along the Ten Mile River.
Neighborhoods
Home to many small businesses, including various restaurants, bars and gift shops!
15 locals recommend
Pawling
Home to many small businesses, including various restaurants, bars and gift shops!
Kent
Just 15 minutes away, Kent offers many restaurants and art galleries.
A bit further of a drive, but a classy old American town. Rich in antique shops and great restaurants.
44 locals recommend
Millbrook
A bit further of a drive, but a classy old American town. Rich in antique shops and great restaurants.
A bit of a trek from Pawling but if you’re up for a few days this is a cool town to check out!
255 locals recommend
New Paltz
A bit of a trek from Pawling but if you’re up for a few days this is a cool town to check out!
Wineries
We have many local wineries! Here are a few of our favorites!
White Silo Farm & Winery
32 Rt. 37 EastBeautiful winery with amazing sunsets. Local secret. 🤫
An outstanding winery located in the heart of Millbrook. We encourage you to do their outdoor wine tasting!
147 locals recommend
Millbrook Vineyards & Winery
26 Wing RdAn outstanding winery located in the heart of Millbrook. We encourage you to do their outdoor wine tasting!
Benmarl Winery
156 Highland AveA nice winery if you plan on heading to New Paltz for the day.
Breweries
Local craft breweries. Most have
outdoor seating and live music on the weekends!
Housatonic River Brewing
30 Kent RdGreat selection of beer and live music!
Sloop Brewing Co. @ the Factory
755 East DrHudson Valley Brewery
7 E Main StAngry Orchard
2241 Albany Post RdA bit of a drive but always worth it!
Traveler advice
Getting around
Travel by Car
The area has a ton to offer and you’re going to want to see as much as possible! Having a car to get around is a must!
Book before you go
Restaurants fill up!
Our favorite restaurants that we recommend always fill up! Make sure you make reservations before going! Especially Old Drovers Inn, White Horse Tavern and McKinney and Doyle!