  Saturday
10:30 am
to
12:30 pm | Windham Farmers’ Market
with Dorraine Scofield, Blu-Raine (Dorraine w/Alana Wyld of Wyld Blu)
Country, Blues | Windham Local
5410 NY-23 MAIN STREET
Windham, NY See Map |
 Swingin’ country, rock and blues featuring Alana Wyld and Dorraine Scofield.
Come on down in the morning for fresh organic produce, honey & maple products, soap, pies & cookies, live music and a lot more!
9am-1pm right beside The Windham Local Public House @thewindhamlocal #farmersmarket #windham #catskills
RAIN OR SHINE!! |
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Saturday
11:00 am | Roger & Lenny
Pop/Soft Rock | NECC Farmers Market
Dutchess Avenue
Millerton, NY See Map |
 A year-round farmers market to increase community access to local, fresh food, provide local producers a sustainable sales outlet, and provide everyone with an opportunity to meet and come together.
There is a wide variety of seasonal produce, pasture-raised meats, fruit, cheeses, baked goods and prepared foods. All of our vendors are local and use sustainable and ethical growing practices. |
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 Saturday
1:00 pm
to
5:00 pm | Wine, Autumn Leaves and Live Music
Rock (classic), Country. Feel good songs everyone loves | Millbrook Vineyards & Winery
26 Wing Road
Millbrook, NY See Map |
| We are back at Millbrook Winery and Vineyards for our thrid year. This is one of our favorte places to play and this should be another great day. Bring your lawn chairs your love of vino and join us!! |
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Saturday
2:00 pm
to
5:30 pm | Hurley Mountain Highway - HMHBand
Pop/Soft Rock, Rock (classic) | Village of Highland Falls Roe Park Pavilion
Roe Park Road
Highland Falls, NY See Map |
 FREE & OPEN TO THE PUBLIC!
Village of Highland Falls 120th Anniversary Celebration!
Roe Park Pavilion (Roe Park Road, Village of Highland Falls, NY)
Relax and enjoy a beautiful sunset and a wonderful night of music among friends...listen, sing, dance, and reminisce!
Rain/shine event... |
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 Sunday
12:00 pm
to
3:00 pm | Darren Read - Solo
Acoustic | Magnanini Winery
172 Strawbridge Rd
Walkill, NY See Map |
 Sunday October 4th I'll be at:
Magnanini Winery 12-3pm
Always a good time come join me 🍷🎸😎✌️
Darren Read Acoustic Solo |
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Sunday
12:00 pm
to
5:00 pm | Second Annual Karen Jam
with XOCH
Multi-genre original, Acoustic, and Alternative | The Academy
33 Academy Street
Poughkeepsie , NY See Map |
 Get ready to throw your hands in the air!!! Join XOCH for an acoustic set at the second annual Karen Jam!!! See all your favorite hair bands from the 80s with a few surprises!! $20 ticket supports The School of Rock Beacon!! |
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Sunday
12:00 pm
to
2:00 pm | Acoustic Brunch
with New Middle Class
Acoustic, Singer-Songwriter, and Multi-genre original | Daryl's House Club
130 Route 22
Pawling, NY, NY See Map |
 Two sets of by award-winning singer-songwriting duo New Middle Class. Playfully serious, heartfelt and slightly bent middle class acoustic pop. Their "adventurously original" songs walk a thin line between the funny and the serious, singing about relationships and current events gone awry, the origin of the universe, life, death, and dessert. No cover.
For reservations and more info |
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 Sunday
2:00 pm
to
4:00 pm | CANCELLED! Free Concert! Music in the Park!
with Dorraine Scofield, Thunder Ridge
Country, Covers, and Dance | Big Indian Park
8280 NY Rt 28
Big Indian , NY See Map |
 Welcome to the gazebo in Big Indian Park! Free music!
Bring your dancing boots and your smiles! There will be food available for purchase.
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Sunday
2:00 pm
to
6:00 pm | Catoberfest 2026, Tony DePaolo’s Electric Gypsies, The Costellos, Marshkings Daughter, The Judith Tulloch Band, The Black Coffee Blues Ensemble
Rock (classic), World, and Blues | Hudson Valley Brewery
7 E Main St
Beacon, NY See Map |
 The 14th Annual Catoberfest will take place on Sunday, Oct 4, 2026, at the Hudson Valley Brewery (7 E Main St, Beacon, NY 12508) from 2pm to 6pm. Come enjoy the fall feline celebration of food, refreshments, music, and kid friendly events to help support Mid Hudson Animal Aid (MHAA), a no-kill, free-range cat sanctuary in Beacon, NY. For more information please visit http://catoberfest.cat . Admission to Catoberfest is free. Beverages and food will be available for purchase at the event with a portion of the sales being donated to MHAA.
Tentative Music Schedule
• 3:10pm - 3:50pm - Tony DePaolo’s Electric Gypsies
• 3:55pm - 4:35pm - The Judith Tullouch band
4:40pm - 5:20pm - Marshkings Daughter
• 5:30pm - 6:15pm - he Costellos
• 6:30pm - 7:15pm - Black Coffee Blues Ensemble
Catoberfest 2026 |
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Sunday
3:00 pm
to
5:00 pm | The Song Circle
with Kati Mac (host)
Singer-Songwriter | BeanRunner Cafe
201 S. Division Street @ Esther
Peekskill, NY See Map |
 Kati Mac is a singer songwriter and 7-time daytime Emmy nominee for best song, with 8 albums of original music.
Steve Chizmadia's songwriting captures a nostalgia and romanticism not often found in folk music. A Grand Prize awardee in the Music to Life Songwriting Competition, Steve is also a three-time finalist in the Kerrville New Folk Competition.
Judy Kass is an award-winning songwriter with soulful vocals, no-nonsense lyrics and a genre-bending exploration of guitar and piano. Her albums have appeared on the Folk DJ List of Top Albums in 2014 and 2016, and her latest release, "New Skin" debuted at #4 on the Folk Alliance Top Albums Chart (7/2025).
Bill Kelly, a singer-songwriter, multi-instrumentalist, and producer, has released five albums and has performed with San Francisco's National Theater of the Deranged, the Baptiste Belly Dance Troupe, Folkfoot, Brother Flower, as Graham Nash in a CSN tribute show, and his own Bill Kelly and the House of Cards.
$10 admission. Call for reservations, 914-737-1701 |
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Sunday
3:00 pm
to
5:00 pm | Country Duo at Wappingers Carnifall
with Way Behind The Sun
Country | Brexel-Schlathaus Park
All Angels Hill Rd
Wappingers Falls, NY See Map |
 Way Behind The Sun (Duo) performs traditional and original country music at the Town of Wappinger Carnifall.
More info |
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Thursday
6:30 pm
to
9:30 pm | David Kraai
Americana, Singer-Songwriter, and Country | Krogh's
23 White Deer Plaza
Sparta, NJ See Map |
 David Kraai swings by this excellent restaurant & brew pub to dole out two sets of fine country folk music! Good times, great food & cold drinks will be going down all evening, so be sure to mosey on over for the hootenanny... |
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Thursday
8:00 pm
to
10:00 pm | Outlander in Concert: Echoes Through The Highlands
Folk/Traditional, Celtic. Film Score | Paramount Hudson Valley Theater
1008 Brown St
Peekskill, NY See Map |
 Outlander in Concert: Echoes Through The Highlands comes to Paramount Hudson Valley on October 8 for the official “Outlander” concert experience. This unforgettable live event brings the global phenomenon to life as a live orchestra performs Bear McCreary’s acclaimed score, curated by showrunner Matthew B. Roberts, alongside breathtaking scenes and highlights from all eight seasons of the series.
Through time, love, and music, audiences will relive Claire and Jamie’s sweeping journey from Craigh na Dun to the New World. With Scotland’s Celtic sound taking center stage, the concert celebrates the romance, legacy, landscapes, and rich heritage that have made “Outlander” a beloved story across the world.
Created in collaboration with Matthew B. Roberts and original Emmy and BAFTA Award-winning composer Bear McCreary, Outlander in Concert: Echoes Through The Highlands is a symphonic love letter to the story that captured millions of hearts.
Event & ticket link |
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Thursday
8:00 pm
to
10:00 pm | Autumn Leaves Party!
with Dorraine Scofield, JB Hunt
Pop/Soft Rock, Country, and Acoustic | Taphouse Grille Windham
5359 Main Street
Windham, NY See Map |
 Check out this cool place with great food, drink, music and fun! Very relaxed atmosphere. |
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David Kraai swings by this excellent center for community enrichment to dole out a concert of the finest country folk music... mosey on out for a fun afternoon of music & merriment! Advance registration is required.
The Poughkeepsie Jazz Project was created in 2012 with the goal of maintaining live jazz culture and community in Poughkeepsie, NY. Since its inception, The PKJP has presented a weekly jazz jam session accessible to all musicians and fans of live music. Over the past twelve years, the jam has been honored to host hundreds of musicians from the Tri-state area. This event is free to both participants and listeners. All with a passion for jazz are welcome.
Friendly open jam - all abilities are welcome!
Private Party 🎉
A new brewery in Washington Hollow with tasty brews, good food, and live music.