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Kick off the summer on June 21st, 2025 when all of Main Street in Little Valley will be closed for the inaugural Little Valley Community Day! Over 30 vendors will fill the street along with food trucks, family activities, children's games, live music, bounce houses and more! The event will run from 1pm until 9pm. This is a rain or shine event.

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.

Ellicottville Distillery will host their 5th annual Distilled & Chilled Music Festival!

Craft Beer, Food Trucks & Craft Vendors Onsite!

Come down to Bicentennial Park on Erie St. in Little Valley Thursday, August 22nd for the final "Music in the Park" this summer hosted by Friends of Little Valley along with a cornhole tournament hosted by $lick $hooters Cornhole! 

Music begins at 6pm, featuring the "Iron Eyes Experience", a local three piece group based out of Salamanca. The band is well known for their rock and blues style that can be heard echoing throughout the enchanted mountains of Cattaraugus County! 

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 into the festive spirit and learn how to create beautiful holiday centerpieces that will impress your guests. An expert instructor Amy, from Swan Street Florist, will guide you through the process, sharing tips and tricks along the way.

Whether you’re a seasoned crafter or a beginner, everyone is welcome to attend. Don’t miss out on this opportunity to unleash your creativity and add a personal touch to your holiday decorations. Grab your friends and family and join them for a memorable workshop! 

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. 

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.