A Day Trip to Pine Plains: 24 Hours in the Dutchess County Town

Autumn view at Dutch’s Spirits in Pine Plains. Photo by Sabrina Sucato

Leave the hustle and bustle of city life behind in favor of country living with top-tier dining and history galore in the Hudson Valley.

Tucked into the northeastern corner of Dutchess County, Pine Plains is one of the Hudson Valley’s true hidden gems. It’s a small town, especially when compared to county hotspots like Beacon and Poughkeepsie. Yet what it lacks in size it makes up in personality. You see, Pine Plains is an under-the-radar hub for some of the top makers and things to do not just in Dutchess County, but in the Hudson Valley as a whole (and beyond).

So are you ready for an adventure? It’s time to hop in the car and cruise on over to Pine Plains for a picture-perfect 24 hours in the Hudson Valley. If you go, don’t forget to tag us @HudsonValleyMag on Instagram! We might just regram you.


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8:30 a.m. – Start the day with a farm-fresh breakfast at Chaseholm Farm

Embrace the countryside vibes from the get-go with a morning meal at Chaseholm Farm in Pine Plains. This Hudson Valley creamery is now in its third generation, and it’s one of the region’s top names when it comes to one-of-a-kind cheese that are #charcuterieboardgoals. For breakfast, stop by the farm store for everything from raw and pasteurized milk to 100-percent grass-fed yogurt. Round the dairy-centric fare out with coffee and a loaf of bread for a snack-style breakfast that’s fresh as can be.

100 Chase Rd, Pine Plains


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9:30 a.m. – Hike your way up the Stissing Mountain Fire Tower

Fire tower hikes are a staple in the Hudson Valley, and Pine Plains has its very own version. After breakfast, head to the Stissing Mountain Fire Tower for a stimulating hike. The trek takes approximately 45 minutes, but feel free to stop along the way for nature-centric photo ops. There are two ways to get to the tower, so choose your own adventure, then prepare yourself to head upwards of 90 feet in order to reach the top. Since the tower sits at an elevation of 1,402 feet near the summit of Stissing Mountain, it offers prime vistas of Connecticut, Massachusetts, and Vermont to the east and Albany to the north on a clear day.

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12 p.m. – Stop for lunch at El Guacamole Mexican Grill

A family-style eatery in Pine Plains, El Guacamole is the perfect spot for a lunch break after an invigorating hike. Dig into a menu filled with go-to classics like taco salads and chimichangas, or switch it up with a vegan guacamole rice bowl or the mouthwatering birria tacos. P.S. The eatery has Mexican sodas on offer, too, so feel free to treat yourself to a refreshing tamarind bubbly alongside your meal.

7795-7797 S Main St, Pine Plains

Dutch's spirits in pine plains
Dutch’s Spirits. Photo by Sabrina Sucato

1:30 p.m. – Dive into history and nature in Pine Plains

After a spot of lunch in town, it’s time to choose whether you’d like to explore the historic or the natural side of Pine Plains (or both!). For nature lovers, Thompson Pond is a must-see. The preserve rests at the base of Stissing Mountain (remember that fire tower hike earlier?), and the pond itself was formed around 15,000 years ago thanks to melting ice over the land. Today, the preserve is home to more than 245 species of land plants and 142 species of wetland plants. During your visit, keep an eye out for migratory birds as you trek along one of the preserve’s trails.

If history is more your thing, don’t pass up a visit to the Graham Brush House, which is led by the Little Nine Partners Historical Society. Check the house’s Facebook page before your visit to see if the venue is open or offering special tours or programming. Also, when in season, make a pitstop to Dutch’s Spirits. The former bootlegging hotspot turned distillery oozes history and Hudson Valley charm. And yes, the drinks here are stellar, too.


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3 p.m. – Go shopping around Pine Plains

Make the most of a day trip to Pine Plains by spending the afternoon popping by the town’s top spots. Since you already visited Chaseholm Farm for breakfast, now’s your chance to swing over to Ronnybrook Farm. While the farm’s address is technically in Ancramdale, it’s located right next to Chaseholm Farm, making it a prime spot to visit. Pick up everything from milk to yogurt, and don’t miss out on the extra-creamy ice cream and, when it’s in season, the locally iconic eggnog.

From there, make a stop at Gallery & Goods to shop the one-of-a-kind goods from talented makers. The shoppable gallery is located inside an historic church, which adds to the experiential nature of the visit. While you’re in the area, dip into Hammertown Barn, one of the region’s top lifestyle and furniture stores. We dare you not to fall in love with at least one of the eye-catching pieces on offer.

Keeping with the housewares theme, Demeter Home is a delight for anyone who loves gorgeously curated storefronts that make you feel right at home. The shop specializes in goods from regional artisans intermixed with ones from luxury, national, and even international brands.


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6 p.m. – Savor fine French fare at Champêtre

This under-the-radar hotspot is well worth the drive to Pine Plains, whether it be as part of a day trip or just because. Start strong with appetizers like escargots de Bourgogne with herb garlic butter or local oyster mushrooms that are flash-fried and gluten-free to boot. For the main course, choose between fish, meat, and vegetarian options, which could be anything from halibut bonne femme to steak tartare to lobster and monkfish risotto. No matter what you order, save room for dessert, which includes mouthwatering dishes like marquise au chocolat and pavlova, among others.

2938 Church St, Pine Plains

7:30 p.m. – Catch a show at The Stissing Center

Named in honor of Pine Plains’ signature mountain, The Stissing Center is a hotspot for cultural to-dos in Dutchess County. While the center itself is relatively new, the building in which it resides is not. Originally dubbed Memorial Hall, the edifice dates back to 1915 and has long been a destination for entertainment and performances in the community. Today, score tickets for everything from classical concerts to spicy tango tunes to moving narratives and plays. Visit the website for a full lineup of upcoming shows.

2950 Church St, Pine Plains

9 p.m. – Spend the night at The Inn at Pine Plains

After spending a full day in town, treat yourself to a relaxing overnight at The Inn at Pine Plains. The charming retreat boasts eight uniquely decorated bedrooms, some of which even come with kitchenettes and additional beds. In the morning, wake up to a sweet continental breakfast spread of locally made bread and coffee, not to mention the inn’s signature breakfast sandwich of local hard-boiled eggs, avocado hummus, organic microgreens, and tomatoes. How’s that for a way to start your day?

3036 Church St, Pine Plains

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