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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 the following dates and times. 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.

See the full schedule of days, times and sponsors.

Celebrate the season with an exciting performance by the Southern Tier Symphony! The Holiday Brass concert brings bold, joyful sounds to ring in the holidays.

Showtime is Friday, December 5th, 2025 at 7:30pm. Tickets are $20 for adults, $18 for senior citizens and SBU staff & faculty, and $5 for students. 

Get in the holiday spirit and unleash your creativity as you decorate delicious cookies with a variety of colorful frostings, sprinkles, and edible decorations. Whether you're a beginner or a seasoned baker, this hands-on workshop is perfect for all ages and skill levels.

During the workshop, you'll learn tips and tricks from Cupcaked Bakery, who will guide you through different techniques to create beautiful and unique designs. It's a great opportunity to spend quality time with loved ones, make new friends, and take home some scrumptious treats to share.

Randolph’s Country Christmas is an annual event. Starting off the day is Randolph Holiday Arts & Crafts Show and the Christmas Magic 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. Browse the vendors along with a concession stand and bake sale.

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.

Discover the joy of skiing and snowboarding with Holiday Valley's Learn to Love Winter event on January 3rd! For anyone ages 4+ who is brand new to snowsports, this beginner-friendly experience is the perfect way to start your winter lifestyle journey!

What’s Included:

HO! HO! HO! The holidays are fast approaching and there's no better way to get into the spirit than by spending some time in Allegany State Park. Join the Environmental Education Department on Saturday, December 6, for a fun, festive, family event – Saturday with Santa! 

In this, the season of giving, we are asking event participants to bring non-perishable food items and/or an unwrapped toy to be donated to a local food pantry and Toys for Tots. This is sure to be a great day! Don't miss out!

With the Thanksgiving holiday less than a week away, Seneca Allegany Resort & Casino is gearing up to start the ensuing holiday season in spectacular fashion.

Get ready to rock and join the fun at Ellicottville Brewing Co. - Little Valley on July 13th from 1-4pm for an unforgettable afternoon of live music with the Iron Eyes Experience! 

Come groove to the sounds of this talented band and enjoy a fun-filled afternoon with friends and family. Whether you're a fan of rock, blues, or just great music, Iron Eyes Experience is sure to bring the energy!

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.