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Join in for the HoliTrot Fall Festival Trail Run! 

Get ready to lace up your running shoes and celebrate the vibrant autumn season at HoliMont! You're invited to the exciting HoliTrot Fall Festival Trail Run, featuring a Kids Race and a scenic 5k trail run through our beautiful trails.

Schedule:

• 10:00 AM - Kids Race
• Immediately Following Kids Race - 5k Trail Run

Race Highlights:

Join in for the HoliTrot Fall Festival Trail Run! 

Get ready to lace up your running shoes and celebrate the beautiful autumn season with HoliMont! This exciting event features a Kids Race and a 5k, winding through their extensive and scenic trail system.

Schedule:

• 9:30 AM - Kids Race
• 10:00 AM - 5k Trail Run

Race Highlights:

Rusty Rooster Farm & Vintage LLC , in Portville is hosting their 5th Annual Harvest Fall Fest on Saturday, October 5th from 10am - 4:00pm. 

The event features FREE outdoor activities like apple cider pressing, fall craft station, doughnuts and funnel cakes, door prizes, a candy count, photo stops, and Live music. 

Inside the shop, there will be in-store specials, honey samples, Ellen's pop up boutique, and a full chocolate shop with grab-and-go specials. 

Come and enjoy the autumn festivities! 

Rusty Rooster Farm & Vintage LLC , in Portville is hosting their 6th Annual Harvest Fall Fest on Saturday, October 4th from 10am - 4:00pm. 

The event features FREE outdoor activities like apple cider pressing, fall craft station, doughnuts and funnel cakes, door prizes, a candy count, photo stops, and Live music. 

Inside the shop, there will be in-store specials, honey samples, Ellen's pop up boutique, and a full chocolate shop with grab-and-go specials. 

Come and enjoy the autumn festivities! 

Want to skip the crowds at Fall Fest? Head just 12 minutes outside of Ellicottville and enjoy a relaxed weekend getaway at EBC Little Valley! Savor craft beer, artisan pizzas, and the beauty of fall while taking in live music all weekend long. 

Live Music Lineup:

Saturday, October 11th - Hazzard County @ 7pm

Sunday, October 12th - The Iron Eyes Experience @ 1pm 

Happy Hour Special: $5 drafts from 2-6pm on both days! 

Stop in for a cozy fall weekend full of good vibes, great beer, and amazing music! 

Ellicottville's Fall Festival is the Village of Ellicottville's largest, most anticipated, autumn event. The village transforms into a walkable 4-block arts and crafts show accompanied by our one-of-a-kind shops, flavorful culinary culture, chair lift rides, live music, and so much more.

Come out to Allegany State Park on October 5th at 9:30am to experience "Autumn in Allegany"! 

This FREE event will be held in the Red House Area of the park at the Administration Building and is perfect for all ages! Participants will learn basic watercolor techniques and create their own masterpieces under the guidance of naturalists. All materials are provided, so you just need to bring your creativity! 

Schedule of Events:

Join "The Scarlet Lily", Ashlie DeArmitt, on November 14th from 6:00-7:00pm for a Fall Floral Arrangement Workshop.

Discover your inner florist this fall by joining this floral arrangement class! Whether you’re just starting out or already have a green thumb, this class provides hands-on instruction to help you create breathtaking floral designs. Master the art of balancing colors, textures, and shapes to make stunning arrangements that will add a touch of beauty to any room.

Cost:

Good Times of Olean will be hosting a Fall Vendor Show Extravaganza on Saturday, November 2nd from 12pm-5pm at Good Times of Olean located at 800 E State St, Olean. 

Admission is free! Come indulge your senses with delicious food & drinks, and great LIVE music while you explore different vendors selling hand made crafts, collectables, and more! Spread the word, rally your friends, and come make some great memories at Good Times of Olean! 

Start your Beer and Wine Festival experience a day early as you Crawl Outta Fall. Guests register in the lobby of the Tamarack Club and pick up a passport that features all the locations to visit for drink specials that evening. Registration takes place between 4 - 7PM and 2 Guys Drinking Beer will be playing music in the Tamarack Club lobby. Only $10 to participate.

Get ready for an unforgettable fall trail adventure on Saturday, October 25th starting at Art Roscoe Trailhead at Allegany State Park.

The Summit 50/50, hosted by Reluctant Runner Racing, is a Trail Sisters approved ultra trail race in the stunning summit of Allegany State Park, New York's largest and most picturesque state park. Experience crisp autumn air, brilliant foliage, and a course that will push your limits in all the best ways. 

Join the Regina A. Quick Center for the Arts in welcoming the Buffalo Philharmonic Orchestra and JoAnn Falletta on Sunday, September 21st, at 3pm.

Expect a powerful performance that promises an evening of moving music and world-class musicianship!

Showtime is Sunday, September 21, 2025 at 3pm. Tickets are $20 for adults, $18 for senior citizens and SBU staff and faculty, and $5 for students. 

Get ready for a cozy Fall Craft Show at the Little Valley Fire Hall on November 15th, 2025, from 11am to 4pm! Enjoy delicious food, shop local, and support talented artisans. 

*Vendor Opportunities:* Interested in showcasing your crafts? Visit (link unavailable) to learn more and secure your spot! 

Mark your calendars and join the fun!

Start your Beer and Wine Festival experience a day early as you Crawl Outta Fall. Guests register in the lobby of the Tamarack Club and pick up a passport that features all the locations to visit for drink specials that evening. Registration takes place between 4 - 7PM and live music will be playing in Edna's at the Tamarack Club. Only $15 to participate.

Photo credit: Holiday Valley Resort