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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. 

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.

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:

Join Ellicottville Distillery on Saturday, May 3rd as they celebrate the Kentucky Derby! They'll be open at 12pm. View the Kentucky Derby live in their tasting room, featuring their own "KenDucky Derby" in their local creek, and live music with The Hick Ups from 3pm-6pm!

Join Ellicottville Distillery on Saturday, May 4th as they celebrate the Kentucky Derby! They will be open at 12pm. View the Kentucky Derby live in their tasting room, featuring their own "KenDucky Derby" in the local creek, and live music with Porcelain Train from 3pm-6pm! Wear your favorite derby hat!

Save the date for a delightful performance form of the the nation's leading classical/jazz cover artists, Willis Delony! This is sure to be a great performance as he collaborates with regional renowned jazz artists. Get ready to soak up a musical evening filled with beautiful melodies.

Showtime is Friday, March 13th, 2026 at 7:30pm. Tickets are $20 for adults, $18 for senior citizens and SBU staff & faculty, and $5 for students. 

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.

Discover the history of Allegany State Park- January 1, 2024. New York's State Parks and Historic Sites celebrates our Centennial in 2024, commemorating the 100th anniversary of the founding of our parks and sites system. Help us kick off this yearlong celebration and get your New Year off to a great start with a hike in Allegany State Park along the newly finished Quaker Run Area Multi-Use Trail.

Rusty Rooster Farm & Vintage LLC , in Portville is hosting their 5th Annual Harvest Fall Fest on Saturday, October 5th 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! 

On Friday, October 25th at 7:00pm, experience an unforgettable evening of music as The Bonnie Raitt Tribute Band takes the stage at the beautifully restored Gowanda Historic Hollywood Theater. 

This talented tribute band brings the soulful voice, bluesy guitar, and heartfelt storytelling of Bonnie Raitt to life, performing her greatest hits and fan favorites with passion and authenticity. Whether your a lifelong fan or simply love live music, this concert is sure to be a night to remember. 

Get ready to rock and join the fun at Ellicottville Brewing Co. - Little Valley on July 13th from 1-4pm for an unforgettable afternoon of live music with the Iron Eyes Experience! 

Come groove to the sounds of this talented band and enjoy a fun-filled afternoon with friends and family. Whether you're a fan of rock, blues, or just great music, Iron Eyes Experience is sure to bring the energy!