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Mother's Day Wine Train

NYLE Train
Celebrate Mother's Day with some wine on a train ride aboard the NYLE Railroad.
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Trivia Night at The Challenger Learning Center

Challenger learning center logo

The Challenger Learning Center announced the return of their popular space quiz event! Join in to test your space knowledge and also support a local organization. The event will feature a quiz with prizes for the winning team. You can participate in a team of 2-5 players.

Apart from the quiz, we will also have raffles with exciting prizes such as a Cutco Block, a $100 gift certificate from the Greater Olean Area Chamber of Commerce, a $50 AMC gift certificate, and more. You can still purchase raffle tickets even if you are not attending the event.

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Showdown Throwdown

Inside Daily City Train
1st Annual Showdown Throwdown Snowboard Event
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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

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 fun events that are perfect for friends and family of all ages, which start the day after Thanksgiving. Start planning your trip!

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.

Float the Allegheny

Friends floating the Allegheny River in Olean area
Float the Allegheny River in a non-timed regatta with music, food and more!
Dates

Holiday Valley Mudslide 2022

Crawling through a giant mud puddle at Holiday Valley's Mudslide
A fun-fun-fun obstacle trail run that's either 3.5 mile or 5.4 mile run with unique obstacles ending with a giant mudslide
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Jingle Bell Jubilee 2023

Horse and carriage ride at the Jingle Bell Jubilee

The Jingle Bell Jubilee is a holiday event featuring many activities and events: the holiday market, carolers, dance groups, wreath creation class, Shop Raffle Drawing, Sips of the Season, make and take craft, horse and wagon rides; an inflated snow globe for picture opps, cocoa and cookie crawl, decorate the tree contest, cookie decorating, and even a Rudolph run! Hours for the event are 4:30-8pm.

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2nd Annual Adult Prom (To Benefit Foster Care)

Woodside Tavern on the Range

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

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HoliMont's Contractor's Day

Skiier at HoliMont

HoliMont Contractor’s Day is an event filled with many fun activities that take place on and off the slopes.  This year’s activities include the 36th annual Dave Pitkin Memorial Ski Race, dedicated to him to commemorate his enduring spirit, his contributions to the HoliMont Racing Club, and his part in creating the racing hill, Our infamous Bombardier Ball Drop, Lunch provided by Dina’s at the Mont, A vendor market, and an Apres Ski Party. This event is sponsored by many local businesses and helps us celebrate and support our local community. Join us for our favorite day of the year!

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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.

Easter Craft Vendor Event

Easter Bunny

Shop through the craft vendors and take your photo with the Easter Bunny!

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The Wildwood Sanitarium

Wildwood Sanitarium, Photo Credit- Amity Photos

The Wildwood Sanitarium opened it's doors in 1906 as a Sanitarium and Bath House. Later, in 1923, it became a Tuberculosis Clinic and then used as apartments later on. 

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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