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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.

Join Jessica Borchert on October 1st from 5:00pm-7:00pm at the Tri-County Arts Council in Olean to celebrate Fall by painting a still life of pumpkins and create an original art piece to add to your fall decor. 

Cost: 

$30 - Artisan Members & Above

$40 - Basic/Family Members & Non-members

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.

Below is a video that highlights the 2016 parade, from the Olean Times Herald, produced by Adam Miller.

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:

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.

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. 

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.

Get ready for an unforgettable fall trail adventure on Saturday, October 25th starting at Art Roscoe Trailhead at Allegany State Park.

The Summit 50/50, hosted by Reluctant Runner Racing, is a Trail Sisters approved ultra trail race in the stunning summit of Allegany State Park, New York's largest and most picturesque state park. Experience crisp autumn air, brilliant foliage, and a course that will push your limits in all the best ways. 

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:

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