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UppenOvr at Holiday Valley

UppenOvr at Holiday Valley 2025

The Most Wonderful Time of the Year

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
Guinness World Record Achieved at Allegany State Park 2014

Fresh off the Press (2014)!
Activities You'll "Fall" in Love With in 2024

College Daze Weekend at Holiday Valley Resort: The Ultimate Snow-Filled Escape

For students craving a break from the rigors of academic life, Holiday Valley Resort's College Daze Weekend is the perfect winter retreat, January 5th-7th.
The Most Wonderful Time of the Year

As snow blankets the majestic peaks, the Enchanted Mountains come alive with the spirit of Christmas! Picture twinkling lights reflecting off frosty pines, cheerful carolers serenading under a starry sky, and the scent of hot cocoa mingling with the crisp winter air.
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.
StrOlean

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.
I Love My Park Day at Allegany State Park

Great Valley Band Jam 2025

Wizards STEAM Night at the Challenger Learning Center!

The Challenger Learning Center in Allegany is hosting a magical event where kids, and parents, can dress up as their favorite wizards and participate in over 30 STEAM activities on October 26th, from 5:30-7:30pm.
Cost: $5 per person
*If you register by October 22nd, your child will receive a special letter from Hogwarts via email that you can print out!
Event Highlights:
StrOlean

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.
Rusty Rooster Backyard Maker's Market

Rusty Rooster Farm & Vintage LLC , in Portville is hosting their 2nd Annual Barkyard Maker's Market on Saturday, July 26th from 10am - 4:00pm.
The event features a ton of vendors, chicken bbq, Live music... and so much more.
For more information and/or updates check out the event on Facebook.
Beach Party at Allegany State Park!

Join in for an unforgettable evening at Red House Beach on Friday, August 15th from 5pm - 9pm!
Event Highlights:
The Holistic Healing & Wellness Fair

You're invited to the Holistic Healing & Wellness Fair in Olean, NY on Sunday, August 17th from 10am until 4pm. This event is free admission!
This event is a full day of healing, inspiration, and high vibes. Whether you're into mind, body, spirit, or just looking for a beautiful day in the park, there is something for everyone.
Here’s what’s waiting for you:
Kids and Adult Fishing Clinic

2nd Annual Adult Prom (To Benefit Foster Care)

Join Foster Cattaraugus for an enchanting evening at the 2nd Annual Adult Prom hosted at Woodside Tavern on the Range on Saturday, August 9th at 6:00pm, benefiting foster care in Cattaraugus County. Don a mask and formal attire for a night of mystery and magic.
Cocktail Hour - 6-7pm, with the event to follow 7-11pm
Dinner - 8pm, provided by Toad's Butcher Shop
Photos - 6-7:45pm, available via donation from April Bojanowski Photography
Comedy Night at Good Times of Olean

Olean's Santa Claus Lane Parade 2025

Come join Santa and Mrs. Claus as they officially light the town's holiday decorations! This festive Annual Santa Claus Lane Parade is held annually on the Friday after Thanksgiving and the traditional kick-off to the holiday season. Santa will be in attendance and light up thousands of lights in Lincoln Park and downtown Olean when he parades through town in celebration.
Final Night of Christmas in Allegany

This is the fifth and final night of Christmas In Allegany at the Allegany Santa House. This is a free event to come visit Santa in his beautifully decorated Santa House with Elf Shack behind selling basket raffle tickets to help support this yearly tradition. Raffle tickets will be drawn after the event.
It's Christmas In Allegany Santa House season!
Visit with Santa and Mrs. Claus at their house in Allegany.
Showdown Throwdown

Little Valley Community Day

Kick off the summer on June 21st, 2025 when all of Main Street in Little Valley will be closed for the inaugural Little Valley Community Day! Over 30 vendors will fill the street along with food trucks, family activities, children's games, live music, bounce houses and more! The event will run from 1pm until 9pm. This is a rain or shine event.
2nd Annual "Ski 4 a Cure"

Autumn in Allegany

Come out to Allegany State Park on October 5th at 9:30am to experience "Autumn in Allegany"!
This FREE event will be held in the Red House Area of the park at the Administration Building and is perfect for all ages! Participants will learn basic watercolor techniques and create their own masterpieces under the guidance of naturalists. All materials are provided, so you just need to bring your creativity!
Schedule of Events:
Christmas in Allegany- Opening Night with Parade

Celebrate opening night of the Allegany Santa House with Santa's arrival by the Allegany Fire Department. This is a free event to come see Santa, and enjoy a beautiful decorated Santa House with Elf Shack containing basket raffles to help support this community event.
It's Christmas In Allegany Santa House season!
Visit with Santa and Mrs. Claus at their house in Allegany.
Additional Dates:
- December 5th
- December 7th
- December 12th
- December 14th
Trivia Night at Challenger Learning Center!

The Challenger Learning Center will be hosting Trivia Night on March 8th, 2025! Doors open at 6:00pm, Trivia starts at 6:30pm!
Come enjoy a night of "out of this world" trivia, Raffles, and a cash bar with 4 Mile Brewing!
This is event is 21+, for more information or to register today, visit https://challengertwintiers.org/upcoming-programs
10th Annual - "Cruising Against Cancer" Car & Craft Show

Mark your calendars for Sunday, May 18th from noon to 4 pm for the 10th Annual Cruising Against Cancer Car and Craft Show located at the Cattaraugus County Fairgrounds! All proceeds will benefit the Roswell Park Alliance Foundation.
This event is rain or shine, in the event of inclement weather, they will move under the barns.
For more information, contact:
- Car Show: Ted Nichols (716-969-3690) or Denny Koch (716-640-0014)
- Craft Show: Sherry Charlesworth (716-244-2344)
Come out and support a great cause!