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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.

Fall into Fun: Paws & Pumpkins 5K 

Join the 2nd Annual Paws & Pumpkins 5K in Little Valley, NY benefiting Empire Animal Rescue Society (EARS)! Whether you're a seasoned runner or a leisurely walker, bring your family, friends, and furry companions for a morning of autumn fun. 

Event Details:

The Greater Olean Area Chamber of Commerce and city leadership are inviting the community out for a night on the town. Working with the city and members of the business community, the Chamber is announcing “StrOlean,” the event aims to bring folks to the downtown shopping district for an evening of fun. 

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.

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.

Gowanda’s Historic Hollywood Theatre proudly presents MR. BRIGHTSIDE!- the ultimate KILLERS experience!

Mr. Brightside: The Ultimate Killers Experience is the premier tribute band from Niagara Falls, NY, delivering electrifying performances of The Killers’ greatest hits. Fronted by Rob Bilson, we bring the iconic sound and energy of The Killers to life!! This show will be held on Saturda, May 3rd at 7 pm.

Tickets $20 - available soon 

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!

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 Greater Olean Area Chamber of Commerce and city leadership are inviting the community out for a night on the town. Working with the city and members of the business community, the Chamber is announcing “StrOlean,” the event aims to bring folks to the downtown shopping district for an evening of fun. 

The Enchanted Mountains Horse Series returns for a full weekend of equestrian action and community spirit. This series offers a fantastic family-friendly atmosphere for competitive riders and spectators alike, featuring a variety of events for all to enjoy.