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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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Run Club with ASP

Pat McGee Trail
May flowers are blooming, so it’s time to get moving!
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Olean Speaker Series- Native American Arrowheads

Olean Point Museum

Join the Olean Historical Society for the 2026 Speaker series, with a presentation by Dana Klein about Native American Arrowheads at 6:30pm on July 20th.

The event will be held outside, so bring your lawn char and meet on the museum's side lawn. If it rains, the event will be held indoors. 

The event will be held at 302 Laurens Street in Olean, NY.

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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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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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Lecture- History & Operations of the PA Railroad

Exhibit at Olean Point Museum

Join the Olean Historical Society for the 2026 Speaker series, kicking off with a presentation by Mike Winicki. He will be speaking on the history and operations of the P.A. Railroad Buffalo Street Yard at 6:30 pm on May 18th.

The event will be held outside, so bring your lawn char and meet on the museum's side lawn. If it rains, the event will be held indoors. 

The event will be held at 302 Laurens Street in Olean, NY.

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Camp Emerald Acres

Camp Emerald Acres
A campground that's the perfect place to enjoy the outdoors with your family or friends.

The Grove

Lobster tails at The Grove
If you are looking for a great dining experience in a charming atmosphere, this is the place for you.

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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West Rose Restaurant

Food to the plates at West Rose Restaurant in Ellicottville
A restaurant with a seasonally-inspired menu of Contemporary-American cuisine, cocktails and a noodle bar!

Learn to Love Winter Lessons

Lessons at Holiday Valley

Discover the joy of skiing and snowboarding with Holiday Valley's Learn to Love Winter event on January 3rd! For anyone ages 4+ who is brand new to snowsports, this beginner-friendly experience is the perfect way to start your winter lifestyle journey!

What’s Included:

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Olean Speaker Series- Fannie Bartlett House

Inside the Fannie Bartlett House

Join the Olean Historical Society for the 2026 Speaker series, with a presentation by Gail Feuchter. She will be speaking on the history of the Fannie Bartlett House at 6:30pm on June 15th.

The event will be held outside, so bring your lawn char and meet on the museum's side lawn. If it rains, the event will be held indoors. 

The event will be held at 302 Laurens Street in Olean, NY.

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Cindy's Craft Co-Op

Outside of Cindy's Craft Co-op in Olean
Shop local, support artisans, and discover the beauty of handmade at Cindy’s Craft Co-Op!

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.