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HoliMont Contractor’s Day is an event filled with many fun activities that take place on and off the slopes.  This year’s activities include the 36th annual Dave Pitkin Memorial Ski Race, dedicated to him to commemorate his enduring spirit, his contributions to the HoliMont Racing Club, and his part in creating the racing hill, Our infamous Bombardier Ball Drop, Lunch provided by Dina’s at the Mont, A vendor market, and an Apres Ski Party. This event is sponsored by many local businesses and helps us celebrate and support our local community. Join us for our favorite day of the year!

Celebrate Earth Day with the Haul Together Community Cleanup on Saturday, April 18th from 8am - 6:00pm. It will be a day of fresh air and local impact across Olean and Allegany. Join the main group on their park-hopping schedule or tidy up a favorite spot on your own time.

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! 

The Challenger Learning Center will be hosting Trivia Night on March 8th, 2025! Doors open at 6:00pm, Trivia starts at 6:30pm! 

Come enjoy a night of "out of this world" trivia, Raffles, and a cash bar with 4 Mile Brewing! 

This is event is 21+, for more information or to register today, visit https://challengertwintiers.org/upcoming-programs 

Join Foster Cattaraugus for an enchanting evening at the 2nd Annual Adult Prom hosted at Woodside Tavern on the Range on Saturday, August 9th at 6:00pm, benefiting foster care in Cattaraugus County. Don a mask and formal attire for a night of mystery and magic.

Cocktail Hour - 6-7pm, with the event to follow 7-11pm

Dinner - 8pm, provided by Toad's Butcher Shop

Photos - 6-7:45pm, available via donation from April Bojanowski Photography

The Jingle Bell Jubilee is a holiday event featuring many activities and events: the holiday market, carolers, dance groups, wreath creation class, Shop Raffle Drawing, Sips of the Season, make and take craft, horse and wagon rides; an inflated snow globe for picture opps, cocoa and cookie crawl, decorate the tree contest, cookie decorating, and even a Rudolph run! Hours for the event are 4:30-8pm.

Rusty Rooster Farm & Vintage LLC , in Portville is hosting their 3rd Annual Barkyard Maker's Market on Saturday, July 25th from 10am - 4:00pm. 

The event features a ton of vendors, chicken bbq, Live music... and so much more. 

For more information and/or updates check out the event on Facebook.

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.

Come down to Bicentennial Park on Erie St. in Little Valley Thursday, August 22nd for the final "Music in the Park" this summer hosted by Friends of Little Valley along with a cornhole tournament hosted by $lick $hooters Cornhole! 

Music begins at 6pm, featuring the "Iron Eyes Experience", a local three piece group based out of Salamanca. The band is well known for their rock and blues style that can be heard echoing throughout the enchanted mountains of Cattaraugus County! 

Join the Olean Historical Society for the 2026 Speaker series, kicking off with a presentation by Mike Winicki. He will be speaking on the history and operations of the P.A. Railroad Buffalo Street Yard at 6:30 pm on May 18th.

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 2nd Annual Barkyard Maker's Market on Saturday, July 26th from 10am - 4:00pm. 

The event features a ton of vendors, chicken bbq, Live music... and so much more. 

For more information and/or updates check out the event on Facebook.

The Seneca Allegany Resort & Casino invites music fans to enjoy the power of classic rock under the stars with an outdoor show featuring Deep Purple, with special guest Kansas on Saturday, August 22nd at 7:30pm. 

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.