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First Day Bike. Next Level Mountain Biking will be leading a ride in the Red House area. Meet at Camp Allegany at 11:00 am on January 1, 2025. The pace and the length of the ride will be moderate and be determined by the participants. Participants may split into different paced groups, if necessary. No one will be left behind. Fat tire bikes are suggested, given the range of conditions likely to be present, however, use your best judgement for the conditions of the day. Questions: Contact Kristian Reiber at 716-785-2685. 

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.

Join the Olean Community Theatre as they present Gilbert & Sullivan's HMS Pinafore, a hilarious comic opera and the story of Josephine, daughter of Captain Corcoran, and her love for sailor Ralph Rackstraw, while being torn between true love and her father's desire for her to marry Sir Joseph Porter, the First Lord of Admiralty. This is sure to be a funny tale of love, honor, and duty. Directed by Jake Riggs with a special arrangement by Concord Theatrics. 

Showtimes at $15.00/person:

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:

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.

Get ready to rev up your engines at the South Dayton Tractor Pull on September 14th, 2025, from 9am-5pm for an action-packed day of tractor pulls, excitement, and fun!  

Don't miss out on the thrill of watching powerful tractors in action!  

General Tractor Pull

• Any year tractor is welcome.
• $5 Admission - Hitch Fee, $10/Class for Pullers
• Scales Open at 10 am - Pull Begins at Noon

Garden Tractor Pull

Get ready for a musical adventure with Olean Community Theatre's production of "Freaky Friday"! This hilarious and heartwarming show, based on the beloved novel by Bridget Carpenter, tells the story of a mother-daughter duo who magically swap bodies and must navigate each other's lives. 

Show Details: 

- Dates: November 5, 6, 7, 8 at 7:30 pm, and November 8 and 9 at 2:00 pm 

- Tickets: $15 per person, available online through the Olean Community Theatre website or at the door 

Olean 1854 is one of two amateur mens soccer teams in Cattaraugus County. Their home games are played at St. Bonaventure University or Olean Intermediate Middle School. The have the following home matches scheduled for 2025:

Olean 1854 is one of two amateur mens soccer teams in Cattaraugus County. Their home games are played at St. Bonaventure University or Olean Intermediate Middle School. The have the following home matches scheduled for 2025:

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 $3.00 skate rental fee.

Special appearance by Santa on December 24th from 12-2pm. Free admission, just a $3 rental fee! 

Sponsored by the Olean Rotary Club.

Join the Olean Community Theatre as they present Andrew Lloyd Weber's 'School of Rock', the Musical. Follow Dewy Finn, an out of work Rock singer and guitarist as he pretends to be a substitute teacher at a prestigious prep school, preparing a band of fifth graders to win an upcoming battle of the bands contest! Sure to be a rocking good show! Directed by Kelly Vaccaro with a special arrangement by Concord Theatrics. 

Showtimes $15/person

July 23rd, 24th, 25th & 26th - 7:30pm

July 26th & 27th - 2:00pm