What to Do in the Hudson Valley This Weekend Sep 20 – Sep 22

Skywalk Arts Fest, Dark Retreat, BBQ, Elton John tribute, DJs, Pizza Concert + more! Something for everyone. Choose your event below…

🌅 Ancram, Fri Sep 20th, 5pm – 7pm. Sunset Sound Bath & Hike.
Join Glendy Yeung for a sunset sound bath and hike at Overmountain. Through mindful prompts and soothing sounds, you’ll connect with nature and yourself! Info HERE.

🎤 Tivoli, Fri Sep 20th, 7pm. Community Sing with Gaia Music Collective at Kaatsbaan Cultural Park.
As part of the 2024 Annual Festival, there will be a free event with the community outside at the Meadow Stage. Seeking to build spaces for people to nurture their relationship with music, whether they’re shower singers, professional musicians, or anything in between! Info HERE.

🪇Saugerties, Fri Sep 20th, 8pm. Samb and Afroflamenco at The Local.
Senegalese musician Sidy Samb, leader of Afroflamenco, blends African roots with flamenco in a unique fusion. After decades in Sevilla, his band unites Senegalese and Spanish artists, featuring vocals, flamenco guitar, balafon, percussion, bass, kora, Cuban tres + dance. Info HERE.

💃 Beacon, Fri Sep 20th, 9pm. YAS DIVA Presents “Marvel Drag Roulette” at The Roosevelt Bar.
Join Andramada, “The Queen of the Hudson Valley,” for an electrifying night of Marvel Drag Roulette featuring the sensational House of Drama at The Roosevelt Bar in the Hudson Valley Food Hall. Info HERE.

🍄 Phoenicia, Fri Sep 20th – Sun Sep 22nd. Dark Retreat, Psychedelics + Virtual Reality: Peril or Promise? at Menla.
This highly experiential retreat explores the opportunities + obstacles in these ancient and modern methods, revealing their potential to accelerate personal + societal transformation. Info HERE.

🧘‍♂️ Woodstock, Fri Sep 20th – Sun Sep 22nd. Fall Equinox Retreat: Kundalini Yoga + Overnight Gong Bath at The V-Hive Woodstock.
Join Hari Kaur and Jenn Drue for a transformative weekend or day-long yoga, meditation + sound healing retreat in the Catskills. Connect with yourself + nature during this special Equinox, honoring life’s cycles and finding inner balance. Info HERE.

🎨 Catskill, Sat Sep 21, 10am – 4pm. Skywalk Arts Festival.
Join us at the Skywalk Arts Festival for stunning Hudson Valley art, live music, and a chance to create your own masterpiece! Info HERE.

🍁Poughkeepsie, Sat Sep 21st, 12:00 pm – 6:00 pm. 24th Annual Arlington Street Fair.
A section of Raymond Avenue is blocked off for this popular annual fest with 100 vendors, inflatable rides, live entertainment, activities for children + more! Info HERE.

🛍️ Woodstock, Sat Sep 21st + Sun Sep 22nd, 12pm – dusk. Octoberfest Mini-Flea at Station Bar & Curio.
They’re cleaning out their “Curio” attic with multivendors, backyard BBQ, beer + brats. Find antiques, oddities, books, pottery, art, vintage leather, tees, lamps, barware + more! Info HERE.

🎶 Rhinebeck, Sat Sep 21st, 12pm – 7pm. Rhinebeck PorchFest Music Festival.
Take a walk down Livingston and Chestnut streets in Rhinebeck and enjoy performances by local musicians playing on front porches everywhere you turn. Info HERE.

🎪 Tivoli, Sat Sep 21st, 3pm – 4pm. PS21 Presents “SANTÉ!” by Cirque Kikasse at Tivoli Memorial Recreation Park.
A lively circus show filled with acrobatics, humor, and jaw-dropping balances—all performed on a unique food truck! The troupe turns furniture into a 30-foot balancing act, creating comic chaos as they clean, bounce on trampolines, and shower the crowd with popcorn. A fun-filled spectacle that will delight kids and spark your inner child! Info HERE.

🖼️ Woodstock, Sat Sep 21st, 4pm. Art Opening at Ever Records.
Patrick Michael Dennis presents “I Exist In You,” a show blending his abstract figurative paintings with live music and a DJ spinning vinyl. Inspired by being a musician, fine artist +  record collector. The exhibit explores the deconstruction of the human body + emotion. Info HERE.

🎧 Woodstock, Sat Sep 21st, 5-9pm, ZIQ STREET at Woodstock Playhouse.
Join us for an epic night with hip-hop pioneers The Last Poets, plus sets from DJ Strafe, reggae artists Rebelle, + DJ Synacure! Info HERE.

🍖 Windham, Sat Sep 21st, 7pm – 9pm. Woodfired BBQ at Eastwind.
Enjoy BBQ buffet with stunning views of Windham Mountain, cooked over Argentinean-style woodfired grills. Info HERE.

🎵Bearsville, Sat Sep 21st, 8pm – late. End of Summer Reggae Party at Tinker Street Tavern.
Live performances from Hudson Valley reggae bands, Caribbean food + drink specials all night! Info HERE.

🎙️ Rosendale, Sat Sep 21st, 8pm. Elton Undressed: Todd Alsup Sings Elton John at Rosendale Theatre.
Flamboyant, soulful, and deeply moving—join NY pop singer Todd Alsup for an intimate acoustic journey through Elton John’s iconic hits. Info HERE.

🍕Accord, Sun Sep 22nd, 7pm – 10pm. A Pizza Party with Wet at Stonehill’s Farmhouse.
Join The Wild Honey Pie + Stereogum for a pizza party concert with a special stripped-down performance by Wet at Stonehill’s Farmhouse. 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!