Gresham Christmas Parties 2026

Participants dress in Santa suits and holiday costumes to ride the SantaCon bus between bars in Gresham. The night includes dancing, food and drink specials, raffles, and costume contests. All ticket and raffle proceeds benefit the nonprofit organization TIP NW.

Guests cruise along the Willamette River taking in views of downtown Portland, the historic Milwaukie waterfront, and the decorated Christmas Ship Fleet. Passengers are seated at reserved candlelit tables and served a freshly prepared three-course dinner alongside live piano entertainment....

Costumed attendees join a massive citywide holiday gathering featuring free cover at more than 20 participating downtown venues. The event includes an Ankeny Alley street closure bar party with live DJs, drink specials, and a singles speed-mingling meetup. Guests can...

Families embark on a holiday cruise along the Willamette River featuring reserved seating and a plated hot breakfast with eggs, bacon, potatoes, pastries, and fruit. Whimsical characters entertain children throughout the voyage with storytelling, music, autograph sessions, and a magic...

Visitors can sample more than 40 regional winter beers and ciders beneath a 75-foot lighted tree. The festival features heated tents to stay warm while vinyl DJs spin music throughout the event.

Guests enjoy a classic Christmas tea experience featuring a plated service with two varieties of tea alongside soup, scones, savory items, and desserts. Following the meal, visitors take a tour of the farm's historic log house.

Guests are seated amongst antique furniture in historic rooms across the mansion for an intimate dining service. The menu features savories by Chef Jorge, pastries from Little Banana Bakery, and artisan teas from Portland's Smith Teamaker. Following the tea service,...

This country music concert features acoustic performances by Bryan Martin, Gavin Adcock, and Trey Pendley, with an opening set by Jacquie Roar. Attendees can hear original music and breakout hits from all three artists together on one stage. Food is...

Participants receive hands-on instruction to bake classic chocolate chip cookies and orange-cranberry shortbread. The class also covers making a spiced cocoa mix and assembling gift packaging for the finished items. All necessary ingredients and materials are provided.