Skip to content

Best things to do in Pawling

Discover the city according to locals. Find the best things to do, places to eat, and get priceless advice from the people who live here.

Bar
“Restaurant and music venue established and owned by Daryl Hall. Great food. Various music/shows on weekends and some weekdays. You can have dinner and a show or just go for dinner. Large bar area as well.”
17 locals recommend
Bakery
$$
“Excellent brunch destination in nearby Pawling, this restaurant has a well-known bakery, fantastic pancakes and omelettes and other brunch delicacies. Gets crowded though, so be prepared to get there early if you don't want to wait for a table.”
18 locals recommend
Restaurant
$$
“Big W's is a destination - it is one of the best BBQ places in NY. Warren (Big W) started as a 5-star chef in NY and moved upstate to escape the city. He started a road-side stand and eventually turned it into a restaurant. ”
5 locals recommend
Bar
2 locals recommend
Cafe
“Breakfast and lunch only. Diner style good food and very reasonable prices. about a 10 minute drive.”
3 locals recommend
Point of Interest
“Access miles of trails through the Pawling Nature Reserve within walking distance of the Blue Bird.”
2 locals recommend
Food
“italian deli meats, cheeses, olives, pasta etc.... nice fresh mozzarella, great green olives...”
3 locals recommend
Convenience Store
Farm
“Pawling Farmer's Market Charles Coleman Blvd Downtown Pawling Saturday's 9:00 - 1:00 p.m. Fresh, organic, local grown produce”
2 locals recommend
Park
“Nice hiking trail that leads to a view over the entire valley -- "Cat rock". Dog friendly!”
2 locals recommend
Gourmet Shop
“Shopping for hostess gifts? Huge selection of artisanal olive oils and balsamic vinegars in many varieties. The recipe board at the front is helpful for foodie ideas.”
3 locals recommend
Point of Interest
“The course is open daily, 7:00 a.m. to Dusk from April to November. NON_RESIDENTS: Weekdays (9 holes/18 holes) Regular $17/$20 Junior $15/$17 League $16/$18 Weekend/Holiday Regular $19/$22 Junior $17/$19 ”
3 locals recommend
Park
“Lake for swimming, tennis, bicycling paths, easy hikes. Live music a few Summer nights. ”
2 locals recommend
Library
“The Akin Free Library is an eclectic destination with a town museum in the top floor and a taxidermy and oddity museum in the basement. Anyone looking for a good distraction on a rainy day should check it out. ”
2 locals recommend
Train Station
“Level of difficulty: Somewhat strenuous Distance and time: 7 miles; at least 5 hours www.nynjtc.org/park/appalachian-national-scenic-trail; www.dutchess.org/hiking/pawling_appalachian_trail It looks like a vintage movie set, but the tiny wooden train platform created specifically for Appalachian Trail hikers, about two miles outside of Pawling, is for real and operates on weekends and holidays. Don’t be fooled: The trail from the train station starts out easy and flat along a lovely wooden boardwalk over Great Swamp wetlands brimming with birds and frogs. Fields and forests follow, but then comes the whammy: a steep ascent to Cat Rocks that is rewarded with pretty, panoramic views. ”
8 locals recommend
Cafe
“Delicious breads, breakfast and lunch items if you are looking for quality, high-end dining.”
2 locals recommend