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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:

Dates
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Red House Lake

Red House Lake by Tim Stockman
Go fishing, swimming or paddling on Red House Lake in Allegany State Park.

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!

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.
Dates
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Embracing Autumn Adventures

Fall Banner

As the leaves start to change and a crispness fills the air, there’s an undeniable excitement that comes with the arrival of fall!

Nash Hill Equestrian Center

Stalls at Nash Hill Equestrian Center
If you're looking for expert horse care or training in a state-of-the-art facility, Nash Hill Equestrian Center is the place for you. 

Manor House B & B

inside by the fireplace

Built in the 1850's, this Historic Homestead is secluded in stately pines on a 130 acre Horse farm. Numerous porches and decks provide relaxing areas to follow the sun and enjoy beautiful sunsets or star gaze.

Great View Cabins

Inside a Great View Cabin
Located near Allegany State Park, Great View Cabins are your ticket to enjoy the beautiful New York woods.

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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Tailgate Thursday

Tailgate Thursday in Olean
A Community Celebration for Football Fans
Dates
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Holiday Valley Resort

Skiers coming down the hill at Holiday Valley Resort
A resort in Western NY for mountain biking, skiing, snowboarding, hiking, golfing, zipline adventure park and more!