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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.

If you’re a first responder, enjoy a free roundtrip train ride from Gowanda, NY, to South Dayton and back. A 30-minute layover in the village of South Dayton lets you explore the vendors in the area, such as farmers, baked goods, and crafts. All first responders ride for free!

• Train Departs at 11:00am & 2:00pm on Saturday
• Train Departs at 2:00pm on Sunday

This Valentine’s Day Tri-County Arts Council will be having a Paper Flower Bouquet class! It’s a perfect activity to do with your girls, and the flowers you make you’ll be able to keep forever. You will create a bouquet consisting of 5 different types of paper flowers and 2 types of leaves. There will be a total of 15 flowers and 7 leaves. Flowers are made by cutting, folding, and gluing different shapes and colors of flowers together. You will need to supply your own small, sharp pointed scissors for accurate cutting of shapes for this class. 

The Enchanted Mountains Horse Series features an exciting game show on Friday nights, and performance classes on both Saturday and Sunday.

Attendees can enjoy a variety of treats from the food concession stand and explore offerings from various clothing and tack vendors. Additionally, each weekend typically includes at least one charitable fundraiser to support a worthy cause or individual in need.

Spectators are always welcome!

Experience Maiden Voyage Live at Gowanda's Historic Hollywood Theater on Saturday, September 13th, 2025, from 6-10pm! 

This is a FREE show, come out enjoy some classic rock and blues and let your troubles drift away. 

Join Ellicottville Distillery for their annual Christmas Tree Bonfire on Saturday, January 17th! 

The doors open at 12 pm. Enjoy live music by Noah Lee from 5pm to 8pm, with the bonfire lighting at around 6 pm. 

Bring your used Christmas trees to add to the pile!

If you love sliding on steel, join us at the Fiddler's Terrain Park on Saturday the 20th for a rail jam that should not be missed. Sponsored by Red Bull, this competition is bound to be action packed and a ton of fun. DJ Tyler Swift will be rockin' the mic and keeping the vibes high!

Call the Fannie Bartlett House to sign up for their Spring Psychic Fair as there are limited spots available. The 2025 Psychic Fair will be held on Saturday, May 17th.

This Queen Anne-style house was originally built in 1881 by George Foreman, and purchased in 1891 by Frank and Fannie Bartlett for $15,000, a hefty sum for that time, he said. The house features nine rooms decorated in turn-of-the-century Victoriana and seven fireplaces, each different in design and composition.

The Olean Theatre Workshop presents, "Every Christmas Story Every Told (And then Some!)" by Michael Carleton, James Fitzgerald, and John K. Alvarez. 

While three actors are tired of performing "A Christmas Story", they decide to take a wild and comedic spin on every beloved holiday tale ever told! This quick paced take through traditions, pop culture, and classic Christmas characters deliver laughter and a needed dose of holiday spirit! 

Join Ellicottville Distillery for their annual Christmas Tree Bonfire on Saturday, January 18th! 

The doors open at 12 pm. Enjoy live music by Tina Williams from 5 pm to 8 pm, with the bonfire lighting at around 6 pm. 

Bring your used Christmas trees to add to the pile!

Randolph’s Country Christmas is an annual event that takes place during the first full weekend of December. Starting off the day is Randolph Holiday Arts & Crafts Show.

Looking for a great opportunity to pick up the perfect one of a kind gift for the holidays?  Randolph Central School is excited to announce the annual RCS Arts and Crafts Show will take place at the High and Elementary School GYMS of Randolph Central School District on Saturday, December 2nd from 10am until 4pm. Browse the vendors along with a concession stand and bake sale.

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. 

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!

Santa Claus will be back in the Town of Olean at his cottage in Lincoln Park on December 13th from 5:30-8:30 pm.

Kids can leave letters for Santa in a mailbox outside his cottage created by families of the EvenStart program. Kids will also receive a small treat from Mrs. Claus!