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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

Come join Santa and Mrs. Claus as they officially light the town's holiday decorations! This festive Annual Santa Claus Lane Parade is held annually on the Friday after Thanksgiving and the traditional kick-off to the holiday season. Santa will be in attendance and light up thousands of lights in Lincoln Park and downtown Olean when he parades through town in celebration.

Below is a video that highlights the 2016 parade, from the Olean Times Herald, produced by Adam Miller.

Join the Olean Community Theatre as they present Agatha Christie's Murder on the Orient Express.

May 14th, 15th, & 16th - 7:00pm

May 17th - 2:00pm

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 the Olean Community Theatre as they present Gilbert & Sullivan's HMS Pinafore, a hilarious comic opera and the story of Josephine, daughter of Captain Corcoran, and her love for sailor Ralph Rackstraw, while being torn between true love and her father's desire for her to marry Sir Joseph Porter, the First Lord of Admiralty. This is sure to be a funny tale of love, honor, and duty. Directed by Jake Riggs with a special arrangement by Concord Theatrics. 

Showtimes at $15.00/person:

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, 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.

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.

Take a trip back in time with a Victorian Christmas at the Fannie Bartlett House in Olean, the Friday after Thanksgiving. Watch the Santa Claus Lane Parade before or after touring this beautifully restored mansion built in 1881 with 15 rooms, including a third-floor ballroom.

The historic house will be adorned with Christmas decorations during its annual open house on Friday from 6-9pm. There will be refreshments and raffle baskets, proceeds to benefit the Bartlett House. 

Olean 1854 is one of two amateur mens soccer teams in Cattaraugus County. Their home games are played at St. Bonaventure University or Olean Intermediate Middle School.

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.