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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! 

Join in for a one day craft show to get into the Christmas Spirit! There will be over 25 different vendors to shop from, where you can find a little bit of everything. It is always a great time to attend a craft and vendor show!

This event is free to the public. You will find a variety of items to shop from! Candles, tumblers, keychains, plants, soaps, baked goods, 3d printed items, crochet and knitted items, and so much more!

There will be over Vendors, Chinese Auction, and food for sale.

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!

Mark your calendars for Sunday, May 18th from noon to 4 pm for the 10th Annual Cruising Against Cancer Car and Craft Show located at the Cattaraugus County Fairgrounds! All proceeds will benefit the Roswell Park Alliance Foundation. 

This event is rain or shine, in the event of inclement weather, they will move under the barns. 

For more information, contact:

• Car Show: Ted Nichols (716-969-3690) or Denny Koch (716-640-0014)
• Craft Show: Sherry Charlesworth (716-244-2344)

Come out and support a great cause! 

Mark your calendars for Sunday, May 17th from noon to 4 pm for the 11th Annual Cruising Against Cancer Car and Craft Show located at the Cattaraugus County Fairgrounds! All proceeds will benefit the Roswell Park Alliance Foundation. 

This event is rain or shine, in the event of inclement weather, they will move under the barns. 

For more information, contact:

• Car Show: Ted Nichols (716-969-3690) or Denny Koch (716-640-0014)
• Craft Show: Sherry Charlesworth (716-244-2344)

Come out and support a great cause! 

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:

Get ready for a musical adventure with Olean Community Theatre's production of "Freaky Friday"! This hilarious and heartwarming show, based on the beloved novel by Bridget Carpenter, tells the story of a mother-daughter duo who magically swap bodies and must navigate each other's lives. 

Show Details: 

- Dates: November 5, 6, 7, 8 at 7:30 pm, and November 8 and 9 at 2:00 pm 

- Tickets: $15 per person, available online through the Olean Community Theatre website or at the door 

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 the Olean Historical Society for the 2026 Speaker series, with a presentation by Dana Klein about Native American Arrowheads at 6:30pm on July 20th.

The event will be held outside, so bring your lawn char and meet on the museum's side lawn. If it rains, the event will be held indoors. 

The event will be held at 302 Laurens Street in Olean, NY.

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! 

Join the Olean Historical Society for the 2026 Speaker series, with a presentation by Gail Feuchter. She will be speaking on the history of the Fannie Bartlett House at 6:30pm on June 15th.

The event will be held outside, so bring your lawn char and meet on the museum's side lawn. If it rains, the event will be held indoors. 

The event will be held at 302 Laurens Street in Olean, NY.

The Olean Theatre Workshop presents, "I Never Saw a Butterfly", a moving theatrical production that honors the memories of children who perished in the Terezin concentration camp in WWII. Based on their poems and drawings, the play showcases their hope, creativity, and humanity amidst unimaginable suffering, serving as a powerful tribute to their legacy. 

Showtimes at $10/ticket

Thursday, May 1st - 7:30pm

Friday, May 2nd - 7:30pm

Saturday, May 3rd - 7:30pm 

Sunday, May 4th - 2:30pm

Join the Olean Community Theatre as they present Andrew Lloyd Weber's 'School of Rock', the Musical. Follow Dewy Finn, an out of work Rock singer and guitarist as he pretends to be a substitute teacher at a prestigious prep school, preparing a band of fifth graders to win an upcoming battle of the bands contest! Sure to be a rocking good show! Directed by Kelly Vaccaro with a special arrangement by Concord Theatrics. 

Showtimes $15/person

July 23rd, 24th, 25th & 26th - 7:30pm

July 26th & 27th - 2:00pm