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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.

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 

Through the generosity of the community businesses and organizations listed below, the City of Olean Youth Bureau & Recreation Department is offering free admission for public ice skating. There is a $3.00 skate rental fee.

Special appearance by Santa on December 24th from 12-2pm. Free admission, just a $3 rental fee! 

Sponsored by the Olean Rotary Club.

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.

Join the Challenger Learning Center in celebrating 15 years of Community Service!

To mark this special occasion, they will be hosting a Chicken BBQ by Carson's and an Open House.

Event Highlights:

Delicious Chicken BBQ ($15)
Open House
Fun Activities for Kids

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.

Today is the day to try before you buy! Free demos from many ski and snowboard reps, featuring Ellicottville's awesome specialty ski and snowboard shops. Check it out, slopeside of the Holiday Valley Lodge. Credit card required for deposit and parent signature if under 18.

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.

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!