HillTap Festival @ Holiday Valley
Full day of outdoor activities and live music from three bands on two stages!
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Cattaraugus County Fairgrounds
Many annual events to see or book a spot for your own event.
I Love New York Winters 2010
This list of activities to enjoy in the Winter was created in 2010.
Ahhh the holidays! Whether you are looking for relaxation or excitement with the holidays we'll have some activities below.
Pat McGee Trail
You may hike, bike, ride a snowmobile or ride horse on this multi-purpose, 12.2 mile trail which connects 7 communities together!
Avoid the Winter Blues
You may think that the winter in the Enchanted Mountains is only for skiiers and snowboarders, but it's not! Check out the variety of events happening for you to enjoy without skis or a snowboard.
Avoid the Winter Blues
Check out the events happening around the Enchanted Mountains in February!
Experience the Magic of NIGHT LIGHTS at Griffis Sculpture Park
Get ready to witness Griffis Sculpture Park in a whole new light this autumn as NIGHT LIGHTS returns for its 13th consecutive year, starting Friday, September 19, 2025.
Experience the Magic of NIGHT LIGHTS at Griffis Sculpture Park
Get ready to witness Griffis Sculpture Park in a whole new light this autumn as NIGHT LIGHTS returns for its 12th consecutive year, starting Friday, September 13, 2024.
Allegany State Park
With over 65,000 acres, this is the largest state park in New York State and is open year 'round with a multitude of outdoor activities for every season and every taste.
Easter Craft Vendor Event
Shop through the craft vendors and take your photo with the Easter Bunny!
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7th Annual Arts & Craft Show
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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Ischua Valley Country Club
A unique golf course, along with a bar and restaurant, bowling (in the winter months) and a golf simulator!
The Haunted Hinsdale House
The Haunted Hinsdale House has a long history of ghost stories!
Olean's Community Wide Garage Sales
The Olean community wide garage sale is a one day event in 2024!
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Randolph's Country Christmas
Randolph’s Country Christmas is an annual event. Starting off the day is Randolph Holiday Arts & Crafts Show and the Christmas Magic 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. Browse the vendors along with a concession stand and bake sale.
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Gowanda's Historic Hollywood Theater
Historic Hollywood Theater in Gowanda.
Winery of Ellicottville
Wine tasting in Ellicottville
Jingle Bell Jubilee
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.
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Randolph's Country Christmas
Randolph’s Country Christmas is an annual event. Starting off the day is Randolph Holiday Arts & Crafts Show and the Christmas Magic 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. Browse the vendors along with a concession stand and bake sale.
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Triple D Rodeo
A rodeo that's fun for the whole family!
The Wildwood Sanitarium
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.
Great Valley Band Jam
A special, big music event with free camping from Friday to Sunday!
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HoliTrot Fall Fest Trail Run
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:
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1st Annual Ohi:yo' Art Market
Immerse yourself in a stunning display of Native American artistry at the 1st Annual Ohi:yo' Art Market! Join in on May 3rd, 2025, at the Seneca Allegany Casino Event Center from 10 a.m. to 5 p.m. Witness the vibrant culture and creativity through exquisite beadwork, pottery, and other traditional crafts. There's something for everyone, making it a perfect outing for the whole family!
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Randolph's Country Christmas
Randolph’s Country Christmas is an annual event. Starting off the day is Randolph Holiday Arts & Crafts Show and the Christmas Magic 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 that the annual RCS Arts and Crafts Show will take place at the High and Elementary School GYMS of Randolph Central School District. Browse the vendors along with a concession stand and bake sale.
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Cattaraugus Rodeo- Bulls & Barrels
High action, live bull and barrel racing!
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Olean's Community Wide Garage Sales
The Olean community wide garage sale is a one day event in 2025!
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Christmas in the Village at Pour Taproom
Join Pour Taproom for "Christmas in the Village."
Kid's can write Santa a letter with some help from the elves and hand it directly to Santa!
Make an ornament for the Children's Hospital and enjoy some hot chocolate.
There will be a Christmas Movie Trivia on Friday at 8pm and an ugly Christmas sweater contest!
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Christmas in Allegany 2023
It's Christmas In Allegany Santa House season!
Visit with Santa and Mrs. Claus at their house in Allegany.
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Manor House B & B
Built in the 1850's, this Historic Homestead is secluded in stately pines on a 130 acre Horse farm. Numerous porches and decks provide relaxing areas to follow the sun and enjoy beautiful sunsets or star gaze.