What to Eat and Where to Go for a Perfect Day in Red Hook

This Dutchess County town has charming shops, scenic landscapes, and the best alternative restaurants in the Hudson Valley.

Wikimedia Commons / Daniel Case

This Dutchess County town has charming shops, scenic landscapes, and the best alternative restaurants in the Hudson Valley.

Drive into Red Hook on a Saturday morning and you’ll have a hard time not falling in love with the Hudson Valley town. Unlike Rhinebeck, its sister city, Red Hook exudes a pleasantly sleepy small town aura. It’s somewhat surprising, considering that Bard College, an internationally recognized liberal arts college, is right next door in Annandale-On-Hudson. Yet Bard students seem to love Red Hook for its quaint charms just as much as locals and visitors do, and for good reason. When it comes to upstate living, Red Hook has it all.

Grilled cheesies + milkshakes with @ehopek ðŸ˜

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9 a.m. — Chow down at Historic Village Diner

No Hudson Valley day trip is complete without a trip to a diner. Fortunately, Red Hook has a roadside eatery that fulfills all your breakfast dreams. Walk through the door of the metallic railroad car edifice and you’ll feel like you journeyed back to the 1950s. Order any of the classics or ask about the daily pastry specials. The gourmet cakes taste even better than they look.

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7550 N Broadway

Open daily 6 a.m. — 9 p.m.

11 a.m. — Stroll along the Poet’s Walk in Red Hook

After a hearty breakfast in Red Hook, get your legs moving on the picturesque Poet’s Walk. The sprawling two miles of trails weave through woods and grassy hills. The Hudson Valley destination is ideal for anyone who enjoys reading from the likes of Wordsworth or Coleridge, since the hillsides look just like a scene from a Romantic poem. Who knows? As you meander along the path, you may be inspired to jot down a stanza or two yourself.

776 River Road


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12:30 p.m. — Stock the pantry at Greig Farm in Red Hook

Red Hook is fortunate enough to house one of the Hudson Valley’s premier foodie farms. Bring the kids to the fields for pick-your-own fruits and veggies to bring home. If you are pressed for time, direct your attention to the farm market instead. The marketplace serves both breakfast and lunch daily and doles out dinner to go. While you’re there, you might even catch an impromptu string concert from some of the valley’s talented performers.

223 Pitcher Lane

Holy cow 😠#icecreamseason

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2:30 p.m. — Experience ice cream magic at Holy Cow

You’ll thank yourself for sticking to a light lunch when it comes time to make the drive to Holy Cow in Red Hook. The unofficial ice cream capital of the Hudson Valley is beloved by all for its low prices and oh so creamy cones. As the days get warmer, don’t be surprised if a (socially distanced) line extends out the door and into the parking lot. The wait is worth the banana split or chocolate dipped cone or hot fudge sundae or, well, you get the picture.

7270 S Broadway Ste 1


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4:00 p.m. — Have a pizza party at Lucoli in Red Hook

Anyone who has lived in the Hudson Valley long enough knows that choosing the “best pizza” in the region is an understandably divisive topic. That’s why it’s a big deal to say that Red Hook’s Lucoli is a serious contender.  The brick oven process, organic ingredients, and in-house mozzarella and sauce preparation help the pies to shine. Try an out-of-the box-option like “Melanzana,” with eggplant and ricotta, or “Cavolo,” with broccoli and tahini for a vegan option

7476 S Broadway


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5:00 p.m. — Devour delectable chocolates at Taste Budd’s Café

With scrumptious chocolates, hot java, and plentiful seating, Taste Budd’s is a community staple in Red Hook and the Hudson Valley as a whole. Throughout the day, the café is a treat to visit. Regional musicians stop in throughout the week when it’s safe to do so to perform everything from folksy tunes to ukulele melodies. Call ahead or visit the shop’s Facebook page to check in on special menu offerings during the week.

40 West Market Street

I’ll be sleeping here tonight.

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9 p.m. — Stay the night at The Grand Dutchess

Whether you live out of state or around the corner in the Hudson Valley, treat yourself to a night at the charming Grand Dutchess. This glorious Victorian inn is a step into the past against the backdrop of an idyllic evening in Red Hook.

7571 Old Post Road

Related: The Best Way to Spend a Day in Poughkeepsie

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