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Weekend Chairlift Rides at Holiday Valley

Family on a summer chairlift ride at Holiday Valley Resort
Summer & Fall Chairlift Rides up the mountain!
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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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2024 Route 16 Yard Sale

Route 16 yardsales from a past year
43 miles of garage sales all along route 16.
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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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2025 Route 16 Yard Sale

A yard sale during the 2014 Route 16 Yard Sale
43 miles of garage sales all along route 16.
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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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Tailgate Thursday

Tailgate Thursday in Olean
A Community Celebration for Football Fans
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A Day in Gowanda

Mural in Gowanda

Tucked into the foothills of the Enchanted Mountains, Gowanda, NY is the kind of small town that surprises you—in the best way. From great food and historic charm to locally made treasures and peaceful countryside drives, it’s easy to turn a simple visit into a full day of fun.

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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Allegany American Legion

Outside view of American Legion
Allegany American Legion, Post #892, offers an Inside Hall as well as an Outdoor Pavillion. Available to non-members as well.