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What to Do in Pawling: How to Spend a Day in Eastern Dutchess

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Photo by Raphael Beretta

From lakeshore picnics to live concerts, this daylong guide to Pawling showcases the Hudson Valley’s natural beauty and vibrant food scene.

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.

 

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9 a.m. – Snag a fresh-baked breakfast at Pawling Bread Co.

Start the day off right with a bite at Dutchess County hotspot Pawling Bread Co. The aromas of this bakery’s morning batches will entice any passersby to move inside. No two visits to Pawling Bread Co. are the same, as the team constantly experiments with new ingredients and pastries. Expect foodie fare like perfect sourdough, black currant scones, or extra flaky croissants. Similarly, the lineup of coffees and teas is made fresh. Try kopi, Malaysian-style espresso with condensed milk, or one of the pastel-colored superfood lattes — bright pink beetroot, soft blue butterfly pea flower, hazy gold turmeric, and creamy green matcha. 

10 E Main St, Pawling
845.493.0562

Pawling Nuclear Lake

Nuclear Lake | Photo by Raphael Beretta

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 with 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, and even plan a picnic. A fresh pastry, creamy latte, and scenic views sound pretty good together. 

Alternatively, check out Cat Rocks for greater heights. A path leads up from the lake, providing a nice incline and plenty of Hudson Valley views. Most importantly, this stretch is a part of the official Appalachian Trail. 

3144 Route 55, Pawling

12 p.m. – Fuel up for lunch at O’Connor’s Public House

Next, enjoy a refreshing beer in Pawling’s own beer garden. O’Connor’s Public House welcomes guests in with open arms and fosters a friendly atmosphere. Few things feel better after a hike than a cold beer and a tasty burger. Approachable pub fare makes for a perfect lunch. Snack on teriyaki flank steak, veggie burgers with goat cheese, and a slew of shareable appetizers. Can’t decide? Opt for the aptly named “Can’t Decide” sampler platter.

6 Broad St, Pawling
845.289.0666

 

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1:30 p.m. – Dive into a good book at The Book Cove

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

 

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3 p.m. – Shop the strip 

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 St, NICÓLJOË sells high-quality men’s and women’s fashion. Any visitor could spend hours popping in and out of this unique collection of small businesses. 

E Main St & Charles Colman Blvd

5:30 p.m. – Sip craft cocktails and dig in at McKinney and Doyle

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-scotch “Campfire in Georgia,” or a tiki-inspired zombie. Diners can order off the small plates menu or go big for supper with Maine lobster risotto 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

 

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7:30 p.m. – Catch a live show at Daryl’s House Club

Music is back 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

Hobbit House

Photo by Jane Haslam Fine Art Photography

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


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