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Monster Truck Rally

Monster Truck Rally at the Cattaraugus County Fair
Come watch the monster trucks in the Grandstands at the Cattaraugus County Fair
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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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Boo Bash

Good Times, Olean

Mark your calendars for the Seven Mountains Media Boo Bash with “The Big Pig, 95.7” at Good Times of Olean on October 26th from 6:00pm to 10:00pm!

Put on your best costume and come out to support the Pink Pumpkin Project while enjoying incredible music from Nashville recording artist Ben Gallaher and Savannah Swatland. Here’s what’s in store:

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Holiday Valley Beer and Wine Festival 2022

Woman pouring a drink at Holiday Valley's Beer and Wine Festival

Beer is Back! The 18th annual Beer and Wine Festival is scheduled for Saturday, November 12th. With many of the region's best craft brewers, wineries and cideries in attendance you can sample your favorites, plus try out several new and unique flavors. Add live entertainment, food trucks and 1500 of your closest friends, it's an event not to be missed.

The format was adjusted so no there are two sessions in order to allow guests to have more space in the lodge. The first session is 1pm - 4pm and the second is 5pm - 8pm.

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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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HoliTrot Fall Fest Trail Run

Runner at HoliMont's Event

Join in for the HoliTrot Fall Festival Trail Run! 

Get ready to lace up your running shoes and celebrate the beautiful autumn season with HoliMont! This exciting event features a Kids Race and a 5k, winding through their extensive and scenic trail system.

Schedule:

  • 9:30 AM - Kids Race
  • 10:00 AM - 5k Trail Run

Race Highlights:

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Beach Party at Allegany State Park!

Red House Beach

Join in for an unforgettable evening at Red House Beach on Friday, August 15th from 5pm - 9pm!

Event Highlights:

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The Pub

Sub made at The Pub
Small-town bar outside of Ellicottville.

Zoar Valley

View at Zoar Valley

Zoar Valley is 2,297 acres of beautiful and dangerous canyon river valley for fishing, hiking, rafting, canoeing and kayaking.

Portville Historical & Preservation Society

Portville Historical Preservation Society

The Portville Historical and Preservation Society is an educational agency, chartered by the Regents of the State of New York. It was established in 1986 in response to renewed interest in the preservation of Portville's past.

Saturday with Santa at Allegany State Park - 2024

Christmas at ASP

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 7th 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! 

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Little Rock City

A view of an area at Little Rock City State Forest.
A local landmark of geologic interest which is located in Rock City State Forest and is accessible in the spring, summer, and fall by vehicle, and during the winter by snowmobile.

Step Right Up at the Cattaraugus County Fair

Fair goers walking through the games at the Cattaraugus County Fair

We think this is the best, small fair with cotton candy, fried food, rides, animal shows, and live entertainment, are all available at the Cattauragus County Fair. Make plans to catch the demolition derby, monster trucks, or a concert. Have some good old fashioned fun! The fair is held yearly, either from the end of July into the first week of August.

Note: Unlike some other county fairs, most of the rides are free with your admission!

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