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12 Skating Days of Christmas 2025

Ice Skating at the William O. Rec Center

Through the generosity of the community businesses and organizations listed below, the City of Olean Youth Bureau & Recreation Department is offering free admission for public ice skating. There is a $4.00 skate rental fee.

Sponsored by the Olean Rotary Club.

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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!

Spring Craft & Vendor Show

Craft and Vendor show

Spring is here and so is the annual spring craft and vendor show! There will be over 35 different vendors to shop from and a chinese auction available. The Lunch Bus, a local favorite food truck will also be at the event! 

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Randolph Retail Company

Randolph Retail Company
A gift shop that offers an eclectic collection of unique gifts, affordable home décor, women’s clothing (teens to Plus sizes), jewelry, and gourmet food.

HoliTrot Fall Fest Trail Run

HoliTrot logo featuring a running turkey

Join in for the HoliTrot Fall Festival Trail Run! 

Get ready to lace up your running shoes and celebrate the vibrant autumn season at HoliMont! You're invited to the exciting HoliTrot Fall Festival Trail Run, featuring a Kids Race and a scenic 5k trail run through our beautiful trails.

Schedule:

  • 10:00 AM - Kids Race
  • Immediately Following Kids Race - 5k Trail Run

Race Highlights:

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Stand-Up Comedy Show

LVFD

The Limestone Volunteer Fire Department is hosting a Stand-Up Comedy Show featuring Robb Will, Jamestown's 67th Funniest Comedian, with special guest Rick Mathews, winner of Buffalo's Laugh Off Competition. 

The show starts at 7:30pm on Saturday, February 14th, 2026. 

Tickets are $25 dollars for non-members and $15 for members. 

Join in for a good time and some laughter presented by Just Vibe Events and Entertainment. 

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Rustic Buffalo

Inside Rustic Buffalo

A vibrant artisan marketplace featuring a wide array of handcrafted goods, home décor, gifts, and specialty foods from local Western New York makers. 

2025 Tame the Tuna Regatta

2023 Tame the Tuna Floaters
Paddle 5.5 miles down the Tunungwant Creek, wear a costume if you'd like and make some stops along the way.
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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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College Daze at Holiday Valley

Skiiers at Holiday Valley

Spend winter break at Holiday Valley with this special lodge and lift package designed for college students. Cost is just $242.48 per person for quad occupancy at the slopeside Inn at Holiday Valley, 3 days and 2 nights lift tickets (start anytime Sunday through 4:30 on Tuesday), an arrival gift, hosted parties, tastings and more. First time skiers or snowboarders get a FREE 1.5 hour lesson, rental equipment and a beginners area lift ticket. College Season Passholders can deduct $100 from their package price. 

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STARS 48th Annual Model Aircraft Fly-In

STARS Fun Fly airshow
See hundreds of radio-controlled aircraft fly through the skies.
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Grace's Field House

Grace's Field House

At Grace's Field House, they specialize in delicious soft serve ice cream, including dairy-free options and refreshing Dole Whip. Choose from their gluten-free or regular cones, and pair your treat with Pepsi products and crispy curly fries.