Cloudcroft's beloved autumn tradition — send your pumpkin racing down the mountain
Every autumn, the steep hill on Swallow Place in front of the Cloudcroft library becomes the stage for one of the village's most beloved traditions: The Great Pumpkin Roll. As the centerpiece of Cloudcroft's annual Harvest Fest, this free family event draws visitors from across the region to watch pumpkins of all sizes go tumbling and crashing down the mountainside. Bring your own pumpkin or grab one at the event, then cheer as they race to the bottom. With categories for both modified and non-modified pumpkins, prizes for winners, and a full afternoon of costume contests, trick-or-treating, free food, and games, Harvest Fest delivers an unforgettable fall day at 8,676 feet.
Pumpkins rolling down Swallow Place
From pumpkin rolling to trick-or-treating, Harvest Fest packs an entire afternoon with activities for the whole family.
The main event! Send your pumpkin racing down the steep hill on Swallow Place. Categories for modified and non-modified pumpkins, with prizes for the winners in each division.
Show off your best Halloween costume on Burro Avenue. Costumes are judged across categories with prizes for the most creative, spookiest, and funniest getups.
Decorate your pumpkin on-site and compete for prizes. Age divisions include 5 & Under, 6-10, 11-15, and 16+. Pumpkin painting also available at the bottom of the hill.
After the costume contest, kids take to the streets of Cloudcroft's charming downtown for trick-or-treating at shops and businesses along Burro Avenue.
The Great Pumpkin Roll and Harvest Fest offer something for every member of the family. All activities are free.
Bring your own pumpkin or buy one at the event. Modified and non-modified categories let everyone get creative with their entry.
Prizes awarded for pumpkin roll winners, best costumes, and pumpkin decorating contest champions across all age divisions.
Warm up with free hot cocoa, hot dogs, and snacks. All refreshments are complimentary at this community celebration.
Free face painting transforms kids into their favorite characters, animals, and spooky creations throughout the afternoon.
Kids can burn off energy in the bounce house while parents enjoy the festivities. Games and a book giveaway round out the fun.
Strike a pose at the Halloween photo booths set up throughout the festival. Capture memories of your family's fall adventure in the mountains.
Everything you need to know to make the most of your Harvest Fest and Pumpkin Roll experience.
Bring your own pumpkin to roll down the hill. A limited number of pumpkins are also available for sale at the event. Both modified and non-modified entries are welcome.
The Pumpkin Roll takes place on Swallow Place (Swallow Drive), the steep hill in front of the Cloudcroft library. From Burro Avenue, head toward the library. Street parking available nearby.
This is a free, family-friendly event with activities for all ages. Kids enjoy face painting, bounce house, games, book giveaway, and trick-or-treating on Burro Avenue.
Pumpkin Roll at 2:00 PM. Costume Contest at 3:00 PM on Burro Avenue. Pumpkin Decorating 3:00-4:00 PM. Trick-or-Treating on Burro Avenue follows the costume contest.
Grab a pumpkin, put on your best costume, and join the fun at Cloudcroft's beloved autumn celebration. Free admission, free food, and a mountain of fall fun for the whole family.