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7th Annual Arts & Craft Show

A past Olean Event at War Vets Park in Olean
Make your way over to the 7th Annual William O. Smith Arts and Craft Show at War Veterans Park in Olean, NY, on Saturday, May 2, 2026.
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Murder Mystery Mayhem

NYLE Train
Participate in a murder mystery train ride with the NYLE Railroad.
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Great Valley Band Jam

Great Valley Band Jam
A special, big music event with free camping from Friday to Sunday!
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Let's Talk Films

Inside Gowanda Hollywood Theater
The Hollywood Theater and Lance Hemlock will have their first session of Let's Talk Film Club
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Great Valley Band Jam 2025

Great Valley Band Jam
A special, big music event weekend with free camping!
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STARS 49th Annual Model Aircraft Fly-In

STARS Fun Fly airshow
See hundreds of radio-controlled aircraft fly through the skies.
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StrOlean

Person enjoying a stroll through walkable Olean

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. 

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Jingle Bell Jubilee

Horse and carriage ride at the Jingle Bell Jubilee

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.

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Saturday with Santa at Allegany State Park 2023

Red House at Allegany State Park

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 2nd for a fun, festive, family event- Saturday with Santa!

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The Most Wonderful Time of the Year

Santa waving during parade in Randolph

It’s time to get into the Christmas Spirit! The Enchanted Mountains has many fun events that are perfect for friends and family of all ages, which start the day after Thanksgiving. Start planning your trip!

November 25th

Christmas in Ellicottville

Tailgate Thursday

Tailgate Thursday in Olean
A Community Celebration for Football Fans
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Brothers Osborne at Seneca Allegany Resort & Casino

Allegany Casino Event Center
One of the hottest duos in Country Music is heading to Seneca Allegany Resort & Casino! The Grammy award-winning Brothers Osborne will take the stage at the Seneca Allegany Event Center on Friday, May 16 at 7 pm.
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Medora Ball Museum

Medora Ball Museum in the Town of Otto
A church that was built in the early 1860's and displays the local history of the Town of Otto.

Alpine Bistro

Cozy atmosphere in Alpine Bistro
A spot for great coffee, small bites, and a cozy space to sit back and unwind!

Gargoyle Park

Disc golf at Gargoyle Park in Olean
A large park in Olean, NY with access to the Allegheny River Valley Trail