What to Do in the Hudson Valley This Weekend Sep 5 – Sep 7

From the Hudson Valley Wine & Food Festival in Rhinebeck to the Oldtone Roots Music Festival in Hillsdale—plus car shows, silent discos, art openings + yoga with llamas—this weekend has all the HV summer vibes! Always a little something for everyone in the Hudson Valley. Take your pick below…

🪕 Hillsdale, Fri Sep 5th – Sun Sep 7th. Oldtone Roots Music Festival at Cool Whisper Farm.
A four-day celebration of roots music, featuring workshops, camping, multiple stages, artisan vendors + late-day jams. Info HERE.

🛍️ Catskill, Fri Sep 5th, 5pm – 8pm. FIRST FRIDAYS in Catskill.
All-day vibes, local sips + snacks, pop-ups, music, discounts + community fun—every First Friday! Info HERE.

🖼️ Saugerties, Fri Sep 5th, 6pm – 8pm. “Rhythm, Fission, and Folds” Opening Reception at Rohmer Gallery.
This exhibition explores transformation through time—cloth as shifting states of mind, music as tension, and discarded materials reborn with new identities. Info HERE.

🎤 Woodstock, Fri Sep 7th, 7pm. Lindsey Webster at Colony Woodstock.
Lindsey Webster’s soaring voice and soulful songwriting have earned her 13 Billboard Top 10 hits. With longtime collaborator Keith Slattery, her new album Music In Me blends jazz roots with fresh R&B energy. Info HERE.

🎸 Beacon, Fri Sep 5th, 8pm. BossaBlue at Towne Crier Cafe.
For nearly a decade, Brad Cole + Bossa Blue has blended jazz, Latin rhythms, rock, soul, and blues into unexpected yet familiar mash-ups—now reimagining James Taylor’s songbook with fresh arrangements rich in melody, groove, and vocal interplay. Read the exclusive interview HERE. Tix HERE.

🚗 Hillsdale, Sat Sep 6th, 9am – 2pm. Hillsdale Classic Car Show at Hillsdale Hamlet Park.
Shiny chrome, roaring engines, and retro rides—classic cars, vintage motorcycles, trucks + campers—plus tacos and live music all day! Info HERE.

🍷 Rhinebeck, Sat Sep 6th + Sun Sep 7th, 11am – 5pm. Hudson Valley Wine & Food Festival at Dutchess County Fairgrounds.
Sip New York wines, craft beers, ciders and spirits. Sample gourmet foods and grab bites from food trucks. Enjoy live chef and mixologist demos all weekend long. More info + tickets HERE.

🦙 Hyde Park, Sat Sep 6th, 1pm – 3pm. Llamaste Yoga + Lavender Loofahs at Clover Brooke Farm.
Enjoy outdoor yoga alongside llamas and alpacas, followed by a hands-on workshop to create your own lavender loofah. Info HERE.

🎨 Gardiner, Sat Sep 6th, 3pm – 5pm. “Botanicals of Mohonk Preserve” Reception at Mohonk Preserve Visitor Center Gallery.
Guided by illustrator Wendy Hollender, five local artists showcase botanical drawings of Mohonk Preserve plants, celebrating the precision of traditional illustration and the rich biodiversity of the Hudson Valley. Info HERE.

🛼 Accord, Sat Sep 6th, 6pm. Roller Derby Bout + Food Drive at Skate Time.
Mid-Hudson Misfits vs Fire Storm face off in a fun-filled night that will bring hard hits, high energy, and community spirit—plus donations support the Regional Food Bank. Info HERE.

🎧 Saugerties, Sat Sep 6th, 8pm – 11pm. Silent Disco at Opus 40.
Live DJs, headphones provided for this fun all-ages dance party! Info HERE.

🎶 Beacon, Sat Sep 6th, 8pm. Songs in the Round at Howland Cultural Center.
An intimate evening of song-sharing, harmonies, and stories with local talents NOGA and Rose Stoller, joined by NYC’s Lila Blue. Info HERE.

🦉 Kingston, Sun Sep 7th, 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.

👢 Kingston, Sun Sep 7th, 12pm – 8pm. Full Moon Honky-Tonk at Westkill Supply.
Learn Texas 2-step, vintage pop-ups + Andrea Madox & the Hey Y’alls playing for you under the full moon! Info HERE

🧶 Kingston, Sun Sep 7th, 2pm – 4pm. Common Threads Fiber Arts Club at Hudson Valley LGBTQ+ Community Center.
Common Threads welcomes all skill levels to explore fiber arts—from knitting and crocheting to sewing, felting, and embroidery—no experience needed. 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.

👉 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!