JACKSON, Wyo. — This December, the Jackson Hole Chamber of Commerce invites Jackson to celebrate community, connection, and holiday cheer during the Shop Local Holiday Weekends, presented by PirateShip.com. Join the Chamber in the heart of downtown each Saturday and Sunday from 1 to 4 p.m. at the Stage Stop building, where holiday spirit is served with a sweet twist: enjoy a free giant sourdough button cookie from Jedediah’s and a cup of hot cocoa — on us!

There’s no better time to show love for Jackson Hole than during the holiday season, and no better way to do it than by shopping locally. When choosing to spend holiday dollars with local businesses, it’s more than checking off a gift list, it’s investing in neighbors, supporting the vibrant community, and helping sustain the small businesses that make Jackson Hole truly one of a kind.

With local roots and a passion for supporting small businesses, PirateShip.com is helping locals and entrepreneurs ship gifts more affordably this season. Their support makes it even easier to celebrate the season with generosity and hometown pride.

Enter to Win Big with Winter Windfall

While shopping locally this holiday season, be sure to register to win a $1,000 shopping spree with Winter Windfall. This exciting holiday raffle offers the chance to win one of five $1,000 prizes, just for shopping locally. With 35 participating businesses, shoppers get one entry for each shopping visit, and the more stops, the better the chances to win.

Here’s the list of participating Winter Windfall businesses:

Support them, and they’ll support you, just as they’ve been doing all year long.

Discover Even More Holiday Magic

The celebration doesn’t stop there. Explore the full calendar of festive happenings by visiting the Western Winter Wonderland webpage. From tree lightings to gallery strolls, musical performances to sleigh rides, Jackson is bursting with opportunities to make new memories this holiday season.

Hosting a holiday event? Chamber members can add it to the Chamber of Commerce calendar for free by submitting it here. Nonmembers are also welcome to participate for a small fee. Help spread the word about all the joy this season brings!

This holiday season, let’s keep the magic close to home. Shop small, give big, and feel the warmth of a community that celebrates together. Happy Holidays from the Jackson Hole Chamber of Commerce!

Experience rustic luxury in this 3-bedroom Hoback Ranches home

by Sponsored by Keller Williams Jackson Hole

A closer look: This 3-bedroom Cottonwood home overlooks Rangeview Park

by Sponsored by The McPeak Group of Jackson Hole Sotheby’s International Realty

A closer look at this 5-bedroom condo at the base of Snow King with great views

by Sponsored by The McPeak Group of Jackson Hole Sotheby’s International Realty

Bordering beautiful Rangeview Park, this home is more than 2,600 sq. ft. with 3 bedrooms, an office and 2.5 baths

by Sponsored by The McPeak Group of Jackson Hole Sotheby’s International Realty

A closer look at this 2-bedroom condo on Powderhorn Lane

by Sponsored by The McPeak Group of Jackson Hole Sotheby’s International Realty