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Grab your Christmas list and meet with Santa and Mrs. Claus! Kids will receive a special treat from Santa.

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!

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!

HO! HO! HO! The holidays are right around the corner, and there's no better way to get into the spirit than by spending a fun-filled day at Allegany State Park for a Saturday with Santa on Saturday December 6th from 11:00am - 3:00pm. 

Join the Environmental Education Department for a festive family event featuring crafts, games, photos with Santa, and plenty of holiday cheer. 

Grab your Christmas list and meet with Santa and Mrs. Claus! Kids will receive a special treat from Santa.

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. 

Warrior Fitness & Wellness will be hosting The Ellicottville Turkey Trot! Start your turkey day with your community at the Ellicottville Turkey Trot! 

Each year this event gets bigger, better, and more fun… and this year will be no exception. Get ready for:

•  A 5K run/walk through beautiful Ellicottville
•  Drinks, snacks, good vibes, and post-run laughs
•  Community, family, and fitness — Warrior style

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.

Feel good this Thanksgiving by starting your day with a non-timed 5K at St. Bonavenure University with other passionate runners and walkers! Continue that feel good feeling by knowing that the registration fee supports the local food pantry and the Every Kid Deserves the Y fund!

Registration is 8:00am - 8:45am at Murphy Hall. Race starts at 9:00am.

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 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

Ready to Roll? Grab your fat bike and join in for a series of Friday night fun rides this winter at Allegany State Park! These casual group rides are the perfect way to get outside, meet other riders, and enjoy the parks beautiful winter trails under the stars! 

Ride Details:

Lincoln Park will be transformed into a holiday haven as the Jingle Bell Jubilee returns on December 13 from 4 p.m. to 8:30 p.m., bringing the magic of a European-style holiday market to the heart of Downtown Olean. This festive event promises fun for the whole family with local artisan vendors, food, drinks, music, and special activities that will make attendees feel like they've stepped into a Hallmark movie.