flea market table with the "Upstate Weekend Plans" text written across the Hudson Valley, NY photo.

What to Do in the Hudson Valley This Weekend Oct 4 – Oct 6

By inside + out | October 2, 2024

There are lots of local end-of-summer happenings to choose from, from a Harvest Hoedown to a Jazz Fest, a Belly Dancing Cabaret, Flea Markets, and more! 🌽 always something for everyone.

🎺 Hudson, Fri Oct 4th – Sun Oct 6th, Hudson Jazz Festival at Hudson Hall.
Immerse yourself in the vibrant fall colors of upstate New York while enjoying a weekend of jazz performances, pop-up shows, and a free Community Day. Info HERE.

🎣 Livingston Manor, Sat Oct 5th, The Catskill Fiberglass Fly Rod Gathering at Dette Flies.
Join Mike McFarland of McFarland Rods, Dusty Smith of Livingston Fly Rods, and the Dette Flies team on 10/5 for an all-day event featuring presentations, a Q&A session, and hands-on opportunities with top fiberglass rods. Info HERE.

🚣‍♂️ Poughkeepsie, Sat Oct 5th, 7:30am – 10:30am. Poughkeepsie Regatta on the Hudson River.
A historic 3-mile race course used by the Intercollegiate Rowing Association Regatta from 1895 to 1949 on the Hudson River. Info HERE.

🍎 New Paltz, Sat Oct 5th, 10am – 4pm. Applestock.
A fall festival full of music, vendors, food, homemade pies + more! Info HERE.

🌾 Woodstock, Sat Oct 5th, 10am – 4pm. Scarecrow Fest at The Comeau.
Join us for a fun-filled family day with scarecrow making, live music, food, free games, arts + crafts and a pumpkin auction featuring local artists. Don’t miss out! Info HERE.

🍁 Highmount, Sat Oct 5th, 10am – 5pm. Fall Festival at Belleayre.
Scenic gondola rides, play in the corn hole tournament, shop through craft vendors, participate in the pie eating contest + more! Info HERE.

🛍️ Rhinebeck, Sat Oct 5th – Sun Oct 6th, 10am – 5pm. Handcrafted Octoberfest at Rhinebeck: A Family Harvest Celebration.
Discover exquisite handmade goods, top Hudson Valley wine and spirits, live music, festive activities, a beer garden, traditional German dancers, and more! Info HERE.

🚜 Stone Ridge, Sat Oct 5th – Sun Oct 6th, 1pm – 6pm. 17th Annual Harvest Hoedown.
Celebrate local agriculture and the harvest season with local food + drinks, live music + dancing and fun activities for adults + kids alike. Info HERE.

🎸Woodstock, Sat Oct 5th, 2pm – 4pm. Woodstock Guitar Sculpture Exhibition + Auction at The Pub.
Iconic wooden guitar sculptures that punctuate the streets of Woodstock all summer long are up for auction in an awesome community event to benefit FAMILY of Woodstock. See you there! Info HERE

💃Kingston, Sat Oct 5th, 7pm – 10:30pm. Luminary Café Cabaret at Arts Society of Kingston.
Get ready for a dazzling night of grace, stunning costumes, enchanting music + a mesmerizing Cabaret Show, followed by an open dance session. Refreshments from MASA MidTown @masa_midtown await—don’t miss this unforgettable evening! Info HERE.

🎸Bearsville, Sat Oct 5th, 8pm. Mdou Moctar at Bearsville Theater.
Mdou Moctar, a Tuareg musician from Niger, grew up in Tchintabaraden and later Arlit, and despite family disapproval of electric music, he built his own guitar with bicycle cables and now performs modern rock inspired by Tuareg guitar traditions. Info HERE.

🪑 Beacon, Sun Oct 6th, 8am – 3pm. Beacon Flea Market.
You’ll find everything + anything such as antique furniture, glassware, vintage designer clothing, vinyl, books, all sorts of jewelry + more. Info HERE.

🦉Kingston, Sun Oct 6th, 9am – 4pm. Red Owl Flea.
First Sundays every month from June – October to hunt for treasure with 20+ vintage sellers, local makers, antique dealers, up cyclers, pickers, collectors, food + more! Info HERE.

🧑‍🌾 Montgomery, Sun Oct 6th, 1pm – 6pm. Out On The Farm: A Queer Fall Festival at City Winery HV.
All ages are invited to spend a fall day at the vineyard with hayrides, pumpkin picking, delicious eats, games, live music, farmstands, and a very special adoption event with the Humane Society of Walden! Info HERE.

👨‍🌾 Explore Hudson Valley’s vibrant Spring to Fall Farmers Markets + CSA, which support small local farms, foster a sense of community, and promote healthy living. From live entertainment to family-friendly activities, they offer a fun and diverse experience for all! Info HERE.