What to Do in the Hudson Valley This Weekend Oct 3 – Oct 5

Cider in hand, crisp air, golden leaves—plus pumpkins, parties, parades + plenty of live music—the Hudson Valley is serving up everything we love about fall this weekend. Take your pick below…

🪶Phoenicia, Fri Oct 3rd – Sun Oct 4th. Sacred Bridge at Menla Retreat.
Uniting the Heart of the Amazon and the Peaks of the Himalayas—sponsored by @tibethouse.us Info HERE.

🎷 Hudson, Fri Oct 3rd – Sun Oct 5th,Jazz Festival at Hudson Hall.
Celebrate jazz and rising stars with world-class performances and free Sounds Around Town shows all weekend. Info HERE.

🛍️ Ghent, Fri Oct 3rd, 1pm – 5pm. Makers Market at Hawthorne Valley
The Makers Market showcases handcrafted goods by artisans, offering a diverse range of items: jewelry, décor, toys, + baked treats. Info HERE.

🍻 Hunter, Sat Oct 4th + Sun Oct 5th, Oktoberfest at Hunter Mountain.
Enjoy local crafts, great food, Scenic SkyRides, live music, and family fun—grab your lederhosen, gather your friends, and celebrate fall in the Catskills! Info HERE.

⚾️ Bovina, Sat Oct 4th + Sun Oct 5th. Vintage Base Ball Festival at the Cowtown Scramble Creamery Field.
Celebrate 200 years of baseball in Delaware County as 11 teams from six states take over the Little Delaware River Valley for a weekend of 19th-century baseball, with games on three fields starting every two hours. Info HERE.

🪩 Kingston, Sat Oct 4th, 11am – 11pm. StockadeFaire in Uptown Kingston.
A day/night of music, community, shopping, and dancing in the streets! Read more HERE. Updates HERE.

🍁 Dover Plains, Sat Oct 4th, 11am – 5pm. The 11th Annual Harvest Festival at Soukup Farms.
Celebrate the season with hayrides, a pumpkin patch, a corn maze, and delicious apple cider donuts. Bring family and friends for a day of fall festivities and create unforgettable memories on the farm.. Info HERE.

🍇 Milton, Sat Oct 4th + Sun Oct 5th, 11am – 6pm. Annual Fall Festival: Leaves + Libations at Nostrano Vineyards.
Local Artisan Market, Live music all weekend, harvest estate wines + more! Info HERE.

📝 Maplecrest, Sat Oct 4th, 11:30am – 9:30pm. Verbatim: Text Sound Expo at Sugar Maples Center for Creative Arts.
An annual Hudson Valley festival of text + sound—showcasing and promoting experimental performances across the region. Info HERE.

🎸 Woodstock, Sat Oct 4th, 2pm – 4pm. Woodstock Guitar Sculpture Exhibition Auction at The Woodstock Pub.
Own a unique piece of art and support a great cause with a preview of the works, live music + auction at 3:30pm. Info HERE.

🌾 Stone Ridge, Sat Oct 4th, 2pm – 6pm. Rondout Valley Growers Association Harvest Hoedown.
Celebrating local farms, harvest bounty, and the community that makes it all thrive—get ready for boots, beats, and bushels of fun. Read more HERE. Tickets HERE.

🍎 Highland, Sat Oct 4th, 2pm – 10pm. Out on the Farm at Bad Seed Hard Cider.
Spend a crisp, queer, fall day (and night) out with cider donuts, apples, pumpkins, live music, a special farm-fresh cabaret + more. Info HERE.

🌝 Wappingers Falls, Sat Oct 4th, 3pm – 12am. Full Moon Gathering at Chapel of Sacred Mirrors.
Ceremony hosted by Allyson Grey + Alex Grey honoring the importance of cosmic alignment, spirituality and creativity. Read more HERE. Event info + Tickets HERE.

🎶 Mount Tremper, Sun Oct 5th, 4pm – 6pm. Sitar Brothers with Subrata Bhattacharya Tabla at Matagiri Sri Aurobindo Center.
Sitarist Deepshankar Bhattachariya, his cousin Rohan Dasgupta, and tabla player Subrata Bhattacharya carry forward renowned musical lineages, blending the Jaffer Khan sitar style with the Farukhabad Gharana of tabla. Info HERE.

🎥 Red Hook, Sat Oct 4th, 5:30pm – 9pm. Vintage Aviation Night Shoot at Old Rhinebeck Aerodrome.
Novice to advanced photographers are invited to this up close and amazing event. Multiple vignettes for your photographic talents to capture in the special nighttime setting. Read more HERE. Info HERE.

🎸 Woodstock, Sat Oct 4th, 7:30pm. Marc Black & Rennie Cantine Celebrate Michael Esposito at Colony Woodstock.
Renny Cantine opening set with Michael Esposito! A lineup of musicians to follow. Read more about this Woodstock Legend HERE. It’s going to be epic! Info + Tickets HERE.

🧛 Kingston, Sat Oct 4th, 8pm – 10pm. The Vampire Circus at UPAC.
This dark, immersive fusion of circus, cabaret, and theater blends acrobatics, dance, illusions, and comedy into a thrilling 90-minute journey through Dracula’s underworld. Info HERE.

🦉Kingston, Sun Oct 5th, 9am – 4pm. Red Owl Flea.
First Sundays every month through November 2nd—hunt for treasure with 20+ vintage sellers, local makers, antique dealers, upcyclers, pickers, collectors, food + more! Info HERE.

🍄 Olivebridge, Sun Oct 5th, 2pm – 4pm. Mushroom Foraging at The Ashokan Center.
Join mycologist Luke Sarrantonio of Mycophilic for a guided hike exploring mushroom ecology, foraging tips, and varieties along Ashokan’s trails. Info HERE.

🚜 Explore Hudson Valley’s vibrant SPRING to FALL Farmers Markets, Marketplaces, and Community-Shared Agriculture (CSA).
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.

Photos by Bob Heuthe

👉 Know of more cool events happening in the Hudson Valley/Catskills area?
Leave them in the comments below.

Have a wonderful weekend from Inside+Out Upstate NY!