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Gargoyle Park

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

Tailgate Thursday

Tailgate Thursday in Olean
A Community Celebration for Football Fans
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I Love New York Winters 2010

This list of activities to enjoy in the Winter was created in 2010.

Ahhh the holidays! Whether you are looking for relaxation or excitement with the holidays we'll have some activities below.

Education in Nature

Path at Nannen
There are plenty of fun and educational activities to do with the entire family in the Enchanted Mountains of Cattaraugus County.

Olean's Music in the Park Series

Gazebo at Lincoln Park
Enjoy music in the park!
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Olean Community Theatre Presents Andrew Lloyd Weber's 'School of Rock', The Musical

Olean Community Theatre

Join the Olean Community Theatre as they present Andrew Lloyd Weber's 'School of Rock', the Musical. Follow Dewy Finn, an out of work Rock singer and guitarist as he pretends to be a substitute teacher at a prestigious prep school, preparing a band of fifth graders to win an upcoming battle of the bands contest! Sure to be a rocking good show! Directed by Kelly Vaccaro with a special arrangement by Concord Theatrics. 

Showtimes $15/person

July 23rd, 24th, 25th & 26th - 7:30pm

July 26th & 27th - 2:00pm

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Music on the Porch at AACCD

African American Center for Cultural Development
The African American Center for Cultural Development invites everyone for Music on the Porch.
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Seneca Sips Beer and Wine Festival

Seneca Allegany Resort & Casino

Join Seneca Allegany Resort & Casino outside for an exciting festival of sips, bites, and local community!

General Admission Sampler- $50
Includes a tasting at each brewery & winery vendor, food tastings, and $20 Free Slot Play.

General Admission Non-Sampler- $35 
Includes food tastings, 2 non-alcoholic drink tickets, and $20 Free Slot Play.

Age 21+ only

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Winter Music Jam

Winter Music Jam in Ellicottville
Three days of indoor live music in all the hot spots, complementing the list of outdoor fun!
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Olean's Music in the Park Series 2025

Gazebo at Lincoln Park
Enjoy music in Lincoln Park!
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Winter Music Jam

Winter Music Jam in Ellicottville
Three days of indoor live music in all the hot spots, complementing the list of outdoor fun!
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Winter Music Jam

Winter Music Jam in Ellicottville
Three days of indoor live music in all the hot spots, complementing the list of outdoor fun!
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Ellicottville Gazebo Series

Ellicottville Gazebo Music Series
Enjoy a live musical performance by some of the region's most talented artists in the village square in Ellicottville.
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The Hickey Tavern

Outside view of The Hickey in Allegany

The go-to dive bar for music lovers! They host touring bands from all around the country and support local music as well!

Pump Boys & Dinettes at Ray Evans Theater

Ray Evans Theater in Salamanca

The Cattaraugus County Living Arts Association is announce their  2025 summer production, the high-energy, crowd-pleasing jukebox musical "Pump Boys and Dinettes"—a toe-tapping celebration of life, love, and laughter on Highway 57!

This production Will Take place on August 8th at 7:30pm, August 9th at 7:30pm, and August 10th at 2pm

A brief synopsis:

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