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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. 

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:

Rusty Rooster Farm & Vintage LLC , in Portville is hosting their 6th Annual Harvest Fall Fest on Saturday, October 4th from 10am - 4:00pm. 

The event features FREE outdoor activities like apple cider pressing, fall craft station, doughnuts and funnel cakes, door prizes, a candy count, photo stops, and Live music. 

Inside the shop, there will be in-store specials, honey samples, Ellen's pop up boutique, and a full chocolate shop with grab-and-go specials. 

Come and enjoy the autumn festivities! 

Randolph’s Country Christmas is an annual event that takes place during the first full weekend of December. Starting off the day is Randolph Holiday Arts & Crafts Show.

Looking for a great opportunity to pick up the perfect one of a kind gift for the holidays?  Randolph Central School is excited to announce the annual RCS Arts and Crafts Show will take place at the High and Elementary School GYMS of Randolph Central School District on Saturday, December 2nd from 10am until 4pm. Browse the vendors along with a concession stand and bake sale.

Get in the holiday spirit and unleash your creativity as you decorate delicious cookies with a variety of colorful frostings, sprinkles, and edible decorations. Whether you're a beginner or a seasoned baker, this hands-on workshop is perfect for all ages and skill levels.

During the workshop, you'll learn tips and tricks from Cupcaked Bakery, who will guide you through different techniques to create beautiful and unique designs. It's a great opportunity to spend quality time with loved ones, make new friends, and take home some scrumptious treats to share.

Portville Central School’s Arts, Crafts, & Antiques Show returns as a one day, indoor event. It will be held at the Portville High School and will feature art, crafts, antiques and food on Saturday, November 2nd from 10:00am-5:00pm.

Proceeds collected directly benefit the students of Portville Central School in the form of achievement awards and student scholarships.

This is the third 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.

It's Christmas In Allegany Santa House season!

Visit with Santa and Mrs. Claus at their house in Allegany.

If you love snowboarding, this is the event for you. Great for spectating! Vendor Village and cookout on the Champagne Sundeck at the Yodeler Lodge. 

Discounted lift tickets for competitors and lodging are available. Assumption of risk form must be signed by a parent if competitor is under 18. 

Photo credit: Holiday Valley Resort

Visit the Fannie Bartlett House for their "Pie on the Porch" event! They will have pie-themed raffle baskets!

This Queen Anne-style house was originally built in 1881 by George Foreman, and purchased in 1891 by Frank and Fannie Bartlett for $15,000, a hefty sum for that time, he said. The house features nine rooms decorated in turn-of-the-century Victoriana and seven fireplaces, each different in design and composition.

It's your time to shine! Join RocketCup Coffee at their Speakeasy at the Cattaraugus Location January 31st at 8pm, for a night of music, laughter, and unforgettable performances at Karaoke Night. Whether you're belting out your favorite ballad or rocking the latest pop hit, the stage is yours!

Enjoy a vast selection of songs to match every mood and style perfect for groups, date nights, or solo stars. Fuel your inner diva with handcrafted cocktails, local brews, and delicious bites from the menu.

Don't miss Songbirds: A Tribute to Fleetwood Mac at the beautifully restored Historic Hollywood Theater in Gowanda on Saturday, October 11, 2025, at 7:00pm. 

Come experience the magic of Fleetwood Mac's greatest hits, performed with passion, authenticity, and powerhouse vocals. From crowd favorites like "Landslide" and "Rhiannon" to rock anthems like "Go Your Own Way" and "Don't Stop", this tribute show captures the spirit and soul of one of the world's most beloved bands. 

The Ellicottville Historical Society invites you to join their Fright Walks on September 27, October 4, October 18, and October 25.