What to Do in the Hudson Valley This Weekend Sep 27 – Sep 29

Stellar happenings in the Hudson Valley: A Sustainable Fashion Show, Garlic Festival, Street Painting Festival, Book Signing, Soundscape + more! 💫 Something for everyone…

👘 Red Hook, Fri Sep 27th, 4pm – 9pm. 2nd Annual Hudson Valley Sustainable Fashion Week at Rose Hill Farm.
A stylish, earth-loving signature organic runway show will begin shortly before sunset with @theGingerWinn playing a dreamy set. BONUS: An afterparty opportunity to meet the makers and shop their runway looks, as well as drink, dance, and be merry. Info HERE.

🎶 Rosendale, Fri Sep 27th, 5:30pm – 7pm. Stone Mountain Sound Collective at the Rail Trail Cafe.
Celebrate falling into Autumn with this trio utilizing improvised + composed music arising from the ground. Info HERE.

🎸Woodstock, Fri Sep 27th, 7pm. Chris Maxwell’s Album Release Show at Colony Woodstock.
Veteran singer-songwriter, acclaimed guitarist, and Clio-award-winning composer Chris Maxwell’s new album, Nothingland, illuminates a troubled, recognizable world. Info HERE.

🧛‍♂️ Rosendale, Fri Sep 27th + Sat Sep 28th, 7pm. Dracula at Widow Jane Mine.
The original Broadway version of Dracula is returning to Widow Jane Mine! Info HERE.

🎧 Hudson, Fri Sep 27th – Sun Sep 29th. Basilica Soundscape at Basilica Hudson.
An immersive + innovative weekend festival showcasing cutting-edge music, conceptual sound performances, art installations, author readings, and curated local vendors, featuring groundbreaking collaborations across music, art, and literature. Info HERE.

🚙 Woodstock, Sat Sep 28th, 9am – 3pm. 14th Annual Woodstock British Car Show at the Woodstock Playhouse.
Join more than 100 British car owners for a smashing display of classic, quirky, and lovable British classics. Info HERE.

🎨 Tivoli, Sat Sep 28th, 10am – 4pm. Tivoli Street Painting Festival.
A vibrant annual event where all ages transform the streets into an open-air gallery with stunning chalk murals. It’s a colorful weekend of art, music, and local culture that brings the village to life. Info HERE.

🧄 Saugerties, Sat Sep 28th + Sun Sep 29th. 10am – 5pm. Garlic Festival at Cantine Field.
In the tradition in which it was born, the Hudson Valley Garlic Festival™ continues to be a fun celebration of the harvest of what garlic aficionados lovingly refer to as the Stinking Rose. Info HERE.

🍇 New Paltz, Sat Sep 28th, 11am – 5:30pm. Grape Stomping Festival at Robibero Winery.
Wine tasting, grape stomping, lawn games, live music, wood-fired pizza + more! Info HERE.

🥁 Kerhonkson, Sat Sep 28th + Sun Sep 29th, 12pm – 9pm. Oktoberfest at Rough Cut Brewing Co.
Two days of live music, delicious German fare, family-friendly fun + more! Info HERE.

🍁 Highland, Sat Sep 28th, 5pm – 9pm. Fall Night Out in Town of Lloyd.
A community pre-holiday shopping, food + music, great drinks + fun. Info HERE.

🩰 Tannersville, Sat Sep 28th, 7pm. Martha Graham Dance Company presents Baye & Asa’s Cortege at The Orpheum Performing Arts Center.
Experience the Martha Graham Dance Company’s stunning new commission by Baye & Asa at the Orpheum, showcasing the magic of their week-long tech residency. Info HERE.

🍺 Shandaken, Sun Sep 29th, 2pm – 6pm. Pig Roast Party at Shandaken Inn.
Shandaken Inn, Catskill Crew + West Kill Brewing are having a Pig Roast Party to celebrate the seasonal changes and the release of West Kill’s Buck Fever Vienna Lager. Chef Bryon will share his Buck Fever BBQ sauce and DJ Harlan will be spinning vinyl. There will also be lawn games, fire pits + more! Info is HERE.

📚High Falls, Sun Sep 29th, 3pm – 5pm. “I Tell Henrietta” with Author Tina Barry & Artist Kristin Flynn at Blue Heron Books.
An afternoon with author Tina Barry + artist Kristin Flynn. Info HERE.

🎻Olivebridge, Sun Sep 29th, 7pm . Karan Casey Trio Concert at Ashokan Center.
Legendary folk and traditional Irish singer Karan Casey, joined by Niamh Dunne on fiddle and vocals, and guitarist and accordionist Seán Óg Graham, will be performing. 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.

Photo by Zio & Sons @zioandsons

👉 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!