Holiday Happenings in Sandy, Oregon: Celebrate the 2026 Season

There’s something special about the holidays in Sandy, Oregon. With the foothills of Mt. Hood as our backdrop, cooler days arriving and downtown getting dressed up for the season, it’s a wonderful time to get out and enjoy our community.

If you’re looking for holiday events and things to do in Sandy, Oregon, there are several fun activities coming up for the 2026 holiday season. From Christmas lights and Santa to trolley rides and holiday markets, here are some dates to put on your calendar.

Sandy Winterfest 2026

One of Sandy’s biggest holiday traditions returns this year! Winterfest 2026 begins December 4 and continues through January 3, 2027.

Meinig Park will be illuminated for the holidays, with lights available for the community to enjoy throughout the season. Winterfest also includes several special events during December.

Christmas Tree Lighting

Friday, December 4 | 5:30–7:00 PM

Kick off the Christmas season with Sandy’s annual Tree Lighting. It’s a great opportunity to get outside, enjoy the lights and celebrate the beginning of the holiday season right here in Sandy.

Winterfest Holiday Markets

December 5, 12 & 19 | 4:30–8:00 PM

Shop locally this Christmas at the Winterfest Markets. The markets feature locally made and inspired goods, crafts, antiques and other items that may help you check a few names off your Christmas shopping list.

Supporting local vendors and small businesses is also a great way to keep holiday dollars right here in our community.

Jolly Trolley Rides

The Jolly Trolley will be running on several evenings during Winterfest:

December 5, 7, 8, 12 & 19

Two rides are scheduled each evening, with the first beginning at 5:00 PM and the second at 6:00 PM.

This is a fun way to experience Sandy during the Christmas season and enjoy some of the holiday atmosphere around town.

Pet Pictures with the Grouch

Friday, December 11 | 6:00–7:30 PM

Even our four-legged family members can get in on the holiday fun. Winterfest will host Pet Pictures with the Grouch for a lighthearted holiday photo opportunity.

Santa in Sandy

Friday, December 18 | 6:00–7:30 PM

Santa is coming to Sandy! Bring the family and enjoy another evening of Winterfest activities.

Shortest Day Walkway

Monday, December 21 | 6:00–7:30 PM

Celebrate the winter solstice and one of the longest nights of the year with Sandy’s Shortest Day Walkway.

Jingle Jog/Walk

Saturday, January 2, 2027 | 9:00–11:30 AM

The holiday fun doesn’t end on Christmas Day. Start the New Year by getting outside for Sandy’s Jingle Jog/Walk.

Make Finding the Christmas Tree Part of the Tradition

Living near the Mt. Hood foothills gives us plenty of opportunities to make choosing a Christmas tree an experience rather than simply another errand.

Several Christmas tree farms operate in and around the Sandy area, including Knapp Farms and Rainy Mountain Farms. Hours, tree availability and seasonal operations can change, so I recommend checking directly with the farm before heading out.

Grab the boots and coats, find the right tree and make an afternoon of it.

Holiday Shopping Close to Home

The holidays are also a wonderful time to support Sandy’s locally owned businesses.

Whether you’re searching for a unique gift, grabbing coffee before heading up the mountain, having lunch downtown or visiting one of the Winterfest Markets, shopping locally helps support the businesses that are part of what makes Sandy special.

The annual Sandy Holiday Craft Bazaar is another local holiday tradition. The event is held the weekend after Thanksgiving and serves as a fundraiser benefiting the Pioneer Boosters, which supports Sandy High School academics, athletics and activities. Check the event organizer’s current information before attending for confirmed 2026 hours and details.

There’s No Place Quite Like Sandy During the Holidays

One of my favorite things about Sandy is that even as our community grows, we still have that small-town feeling. The holidays really bring that out.

You can see neighbors at the tree lighting, shop from local vendors, take a trolley ride, visit Santa, pick out a Christmas tree and enjoy the lights — all without traveling far from home.

If you’re new to Sandy, thinking about moving here, or already fortunate enough to call the Mt. Hood area home, I hope you have an opportunity to get out and enjoy some of these local traditions this holiday season.

Happy Holidays from Sandy, Oregon!