Weekend Getaways in Upstate New York: Where Jazz Meets Nature

There’s something magical about driving north from New York City, watching the skyscrapers shrink in your rearview mirror as rolling hills and vineyards take their place. 

However, here’s a secret most people end up missing—it’s home to a significantly vibrant jazz scene that would make Harlem proud, tucked away in barns, lakeside lodges, and even old churches. So, Upstate New York isn’t just about fresh air and apple picking. 

Whether you’re in Upstate New York for the first time or just visiting from another part of New York, here’s how you can plan a day with waterfall hikes and end it with unforgettable late-night jazz sessions. Make weekend getaways in Upstate New York unforgettable. 

Friday Night: Settling Into the Rhythm

Hudson Valley: Where Jazz Lives in the Hills

Check into The Rivertown Lodge in Hudson—a converted movie theater where each room comes with a vintage record player and a stack of classic jazz vinyl. 

At 7:30 PM, head downstairs where the lobby bar serves Hudson Highballs (local whiskey, maple syrup, and a dash of apple cider vinegar) to the sounds of a live piano trio.

Jazz in the Barn

At The DeBruce, a farm-to-table inn near Livingston Manor, Friday nights mean “Supper & Sounds.” Local jazz musicians play in the 19th-century barn while you dine on hyper-local fare. Add to it the acoustics in that wooden space for a heavenly experience! It’s one of the top weekend getaways in Upstate New York.

Saturday Adventures: From Waterfalls to Walking Bass Lines

Start your day with the Kaaterskill Falls hike. Plan to start the hike by at least 8 AM, as this way, you’ll have the misty cascade mostly to yourself. On your way back, stop at Circle W Market for their famous breakfast sandwich (egg, sharp cheddar, and house-made sausage on a biscuit) that will make the perfect ending of a nutritious meal after your memorable hike!

After that, you can go hiking at Catskill Park and have delicious food in one of the restaurants that serves food made from fresh local ingredients. 

As the sun sets, make your way to The Falcon in Marlboro. This riverside venue has no cover charge—just an honor system where you pay what you feel the music was worth. The soundboard was designed by the same engineer (Tony Falco) who did the Village Vanguard’s. Order the “Falcon’s Flight” cocktail (bourbon infused with black tea) and settle in—the second set (around 10:15 PM) is when things really heat up.

Sunday: Lazy Mornings & Hidden Jazz Gems

Brunch with a Beat

The Village Cafe in Tannersville does Sunday jazz brunch right—their house band plays cool jazz while you dig into lemon ricotta pancakes. The trombonist doubles as the maple syrup sommelier (yes, that’s a thing here).

One Last Musical Surprise

Before heading back to the city, stop at Opus 40 in Saugerties. This massive outdoor sculpture park often hosts impromptu jazz quartets among the stone labyrinths. Check their chalkboard at the entrance—if it says “Music @ 2,” cancel your evening plans.

Insider Tips for Jazz Lovers

1. The Secret Session: At The Avalon Lounge in Catskill, musicians often gather after last call (around 1:30 AM) for informal jams. The bartender will wink if it’s happening.
2. The Unexpected Venue: St. Gregory’s Church in Woodstock hosts “Jazz Vespers” every third Sunday—imagine Coltrane-style improvisation echoing through the nave.
3. The Collector’s Spot: Hudson Valley Vinyl in Beacon has a “jazz basement” where they test rare finds on a 1959 Voice of the Theater sound system.
4. The Roadhouse: The Colony in Woodstock looks divey but books serious talent—their Monday night jam sessions have featured players from Wynton Marsalis’ band.

Final Thoughts

This isn’t just another weekend getaway guide. It’s your backstage pass to the living, breathing jazz scene that keeps Upstate New York’s creative spirit alive—all within a tank of gas from the city. 

Pack your hiking boots and prepare for weekends where adventure meets music and the music flows as freely as the craft cider. So, the next time you want to plan a weekend, remember these top recommendations on things to do in Upstate New York on weekends!

The best way to experience everything jazz is to book a jazz tour, preferable from an experienced local jazz tour operator, like Big Apple Jazz Tours. 

Book a private jazz tour to get the best experiences that extend beyond jazz and create memories for a lifetime.