Upstate NY Road Trip Itinerary! 3 Towns in 3 Days

Buckle up, road trippers! Here’s your perfect itinerary for an Upstate New York adventure through three charming towns- Peekskill, Rhinebeck, and Hudson.

I recently did this exact trip, stopping in all these towns as I went over three days. I loved this trip because everything is within 2-3 hours of the NYC area, making it a perfect weekend getaway.

🌇 Peekskill: First stop, the hidden gem! Peekskill is on the northern end of Westchester, and people often mistake it for the Hudson Valley. Artsy vibes and friendly locals! Stop at Bean Runner Cafe for breakfast and Peekskill Coffee House for coffee.

Bean Runner Cafe

The Peekskill Coffee House

🏰 Rhinebeck: a charming village located in Dutchess County, filled with historic architecture, boutique shops, and delicious restaurants. I savored some coffee and a browning at Bread Alone, which is a local New York coffee chain founded nearby. Another unique activity is picking flowers at Brittany Hollow Farm!

Bread Alone Bakery

Brittany Hollow Farm

🌆 Hudson: Last but not least, the hippest destination! This town is fortunate to have a thriving arts scene, antique shops, restaurants, and historic buildings. I had a great time at Rev Coffee and Hudson Roastery, two great coffee shops in town! We also loved eating at Grazin’ Spirits (vegan friendly) and Le Gamin.

Hudson Roastery

Rev Coffee

Grazin' Spirits - Tasting Room & Restaurant

Le Gamin Country

In short- Scenic drives, picturesque landscapes, and culinary delights unite on this road trip! Save for future travels.

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