Pawling is a Hudson Valley gem. Sheltered partly by bucolic equine farms and gorgeous stretches of the Appalachian Trail, this eastern Dutchess County village has a lot to offer weekenders and day-trippers alike. Visitors to the relaxing retreat enjoy swimming in the summer and colorful walking trails all autumn long. To make the most of a visit, mix retail therapy with sampling local favorites. In a place where natural beauty and entertainment abound, Pawling always has guests yearning for their next trip.
9 a.m. – Sip an espresso-based drink at Dancing Bear Cafe
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A newer addition to the town of Pawling, Dancing Bear Cafe is all about “more of what makes you happy.” From the colorful cafe décor to the upstairs dining space, this cheerful spot is worth a visit for breakfast, lunch, pastries, coffee, and freshly baked bread. Start your morning off with the Brown Bear Latte — or make it a mocha with the Black Bear Latte — then go for the Breakfast Bear-ito for eggs, beans, bacon, cheese, and ranchero sauce in a wrap to fuel your day.
10 East Main St, Pawling
845.493.0931
10 a.m. – Take a scenic stroll around Nuclear Lake
Nuclear Lake’s ominous name does not do its incredible beauty justice. Just off the Appalachian Trail sits a smaller walking route around the shimmering lake. An easy two-mile stroll grants through-hikers an unparalleled view of the lake. Above all, the path is perfect for families with its kid-friendly intensity and opportunities to swim. Relax lakeside on a blanket or even plan a picnic. A fresh pastry, creamy latte, and scenic views sound pretty good together.
Alternatively, check out Dover Stone Church Preserve in Dover Plains for an unbeatable cave hike. Although a few miles up the road from Pawling proper, this 174-acre public preserve features more than four miles of hiking trails and a natural rock formation aptly named Dover Stone Church for its Gothic-style archway.
12 p.m. – Fuel up for lunch at The Turk
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If you’re looking to try something new for lunch, head to The Turk for all the Turkish food you can stomach. The restaurant is newer to the Pawling area, but its Mount Kisco counterpart has been around for years, withstanding the test of time. Dine in for small plates like baba ghanoush, artichoke hummus, lebni, stuffed grape leaves, and feta cheese spread, then fill up on chicken shawarma, spinach borani, kebabs, and falafel. On your way out, grab baklava or baked halva to end things on a sweet note.
42 Charles Colman Blvd, Pawling
845.723.3514
1:30 p.m. – Dive into a good book at The Book Cove
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Feeling a little sluggish after lunch? Cozy up with a good book from The Book Cove. This delightful nook carries both new releases and classics long out of print. A knowledgeable staff can help visiting bookworms find their next engaging read. The Book Cove joins a host of other proudly independent bookstores in the Hudson Valley. As a result, the Village of Pawling has its own cultural hub.
22 Charles Colman Blvd, Pawling
845.855.9590
3 p.m. – Shop the strip
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Pawling’s eclectic “main street” area is chock full of interesting stops. Visitors can up their home salads with gourmet olive oils and vinegars from The Blue Olive. Next, shoppers find their inner child at The Imperial Castle, a vintage-meets-modern toy store. The classic collection is a nostalgia fest, and the shop has plenty of new releases for the kiddies. Further onto East Main Street, NICÓLJOË sells high-quality women’s fashion. Any visitor could spend hours popping in and out of this unique collection of small businesses.
East Main St & Charles Colman Blvd
5:30 p.m. – Sip craft cocktails and dig in at McKinney and Doyle
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No trip to Pawling would be complete without dinner at McKinney and Doyle. The creative cocktail program is worth the visit on its own. Try spicy mango margaritas, the peachy-mezcal “Fire in the Sky,” or the blackberry-ginger “Bulleit Proof.” Diners can order off the small plates menu for key lime shrimp, duck confit bao buns, and buffalo cauliflower or go big for supper with Maine lobster risotto, mushroom carnitas rigatoni, or an ultimate wagyu burger. Lastly, desserts from the adjacent bakery are known throughout the region, especially the artisanal cakes.
10 Charles Colman Blvd, Pawling
845.855.3875
7:30 p.m. – Catch a live show at Daryl’s House Club
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Live music is a big deal in the Hudson Valley, and Pawling has an iconic venue up its sleeve. Head a few minutes down the road from dinner to Daryl’s House Club. Daryl Hall — yes, that Daryl Hall — renovated the space seven years ago and converted it into a home for his Live from Daryl’s House TV show. Check the website for a full calendar of concerts and, if you’re lucky, catch a glimpse of the Hall and Oates legend.
130 Route 22, Pawling
845.289.0185
9:30 p.m. – Settle Into a real-life Hobbit House
Finally, tuck in for the night at any Lord of the Rings fan’s dream getaway. Hobbit Hollow is the Bilbo Baggins abode carved into a quaint hill. Its creators (and hosts on Airbnb) meticulously recreated the experience of a home in The Shire — but don’t worry, it’s not hobbit-sized.
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Alternatively, stay right in town at the Station Inn Pawling. This boutique inn is full of country charm while curating a modern, stylish experience. Visitors looking to stay in the heart of Pawling can find their room just a two-minute walk from McKinney and Doyle.
7 Memorial Ave, Pawling
845.266.6262
Related: Livingston Manor Day Trip Guide: How to Spend 24 Hours in Town
