Rally the corgi has sniffed out the Christmas events for kids in Milwaukie for 2026. Kids decorate umbrellas and march to the tree lighting at historic City Hall on Saturday, December 5, and families watch the Christmas Ships from Milwaukie Bay Park on Saturday, December 19. We check every date on the host’s own website and link straight there. For the rest of the state, see our Oregon Christmas events for kids guide.
What Rally found in Milwaukie
- 2 Christmas events for kids in Milwaukie
- Umbrella Parade and Tree Lighting: Saturday, December 5, parade at 4:30 pm
- Kids prizes for decorated umbrellas, free cocoa
- Winter Solstice and Christmas Ships: Saturday, December 19, 4:30 to 7:30 pm
- Every date checked on the city calendar on Nov 11
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Free Christmas events for kids in Milwaukie
Umbrella paradeFree
Umbrella Parade and Tree Lighting
- When: Saturday, December 5, 2026, 4 to 6 pm (parade at 4:30 pm, tree lit after the winners are announced around 5:30 pm)
- Where: South Downtown Plaza to historic City Hall, Main St., 10722 SE Main St., Milwaukie, OR 97222 (opens in maps)
- Cost: Free
- Ages: All ages
Expand to see the parent tip
Milwaukie’s quirky holiday tradition has everyone decorate an umbrella and march four blocks up Main St. from the South Downtown Plaza to historic City Hall, with no sign-up needed.
Kids can enter the contest in categories like Most Creative, Most Festive and Most Milwaukie, with prizes for children and adults plus best decorated bicycle. The tree is lit around 5:30 pm, and the Rotary Club hands out free treats, hot chocolate and cider.
Parent tip: Contest entrants must line up behind their category sign at the plaza near the post office, 11222 SE Main St., by 4:15 pm.
- Host
- City of Milwaukie (opens in a new tab)
- Address
- South Downtown Plaza to historic City Hall, Main St., 10722 SE Main St., Milwaukie, OR 97222 (opens in maps)
- Confirmed
- On the host’s page, checked
New Milwaukie events every week
Rally researches Christmas events in Milwaukie daily and updates this page with new events. Enter your email to get a weekly update with new events in Milwaukie.
Free. Unsubscribe anytime. Privacy policy (opens in a new tab)
Rally’s Christmas research
Rally the corgi has 1 more Milwaukie event researched for you.
- New events every week We research new events daily and send you one email a week with the new ones we find in Milwaukie.
- Exclusive access to free events Find the free Christmas events in Milwaukie before they fill up.
- Unlock the filters Find Santa visits, free events and weekend plans in one tap.
- Rally’s Christmas Eve Express and a free advent calendar Get early access to Rally the corgi’s Christmas Eve tracker, plus a free digital advent calendar to count down to Christmas.
- One-tap add to calendar Save any event to your Google, Apple or Outlook calendar so you never miss it.
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- 1 Parades
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Christmas Ships viewingFree
Winter Solstice and Christmas Ships
- When: Saturday, December 19, 2026, 4:30 to 7:30 pm (per the city calendar; the ships pass the bay twice)
- Where: Milwaukie Bay Park, 11211 SE McLoughlin Blvd., Milwaukie, OR 97222 (opens in maps)
- Cost: Free, food for sale
- Ages: All ages
Expand to see the parent tip
Families gather at Milwaukie Bay Park to watch the lit-up Christmas Ships parade along the Willamette, warming up by a bonfire between sailings.
Neighborhood associations sell hot dogs, chili, pie and hot chocolate as fundraisers, and large tents keep the crowd dry if it rains. The boats come through Milwaukie Bay twice during the evening, so there are two chances to see them.
Parent tip: Bring cash or a card for the fundraiser food, and check the Christmas Ships schedule the day of in case sailing times shift.
- Host
- City of Milwaukie (opens in a new tab)
- Address
- Milwaukie Bay Park, 11211 SE McLoughlin Blvd., Milwaukie, OR 97222 (opens in maps)
- Confirmed
- On the host’s page, checked
New Milwaukie events every week
Rally researches Christmas events in Milwaukie daily and updates this page with new events. Enter your email to get a weekly update with new events in Milwaukie.
Free. Unsubscribe anytime. Privacy policy (opens in a new tab)
We check every event above on the host’s own page for the date, time and cost, plus the things parents ask about, like sign-ups and ages. Looking for a Santa train instead? Those are on our Oregon Christmas train rides page.
See every event on a December calendar
Plan your December
When each Milwaukie Christmas event for kids happens
Spend an afternoon before December 5 decorating umbrellas with the kids, then save December 19 for the Christmas Ships and a bonfire by the river.
- Umbrella Parade and Tree LightingMilwaukie · Dec 5
- Winter Solstice and Christmas ShipsMilwaukie · Dec 19
Looking further afield? Our Oregon Christmas events for kids guide lists every confirmed event in the state, and we have city guides for Portland, Woodburn, Salem and Eugene. The national search sorts every event by distance from your town.
A story for the drive home
A morning with Santa or an evening of holiday stories tends to end the same way: tired kids, a long drive and one more book before bed. Our picture book follows Rally the corgi on his first train ride to see his grand-paw-rents, and every page is painted by hand. If your family is spending December missing someone, it was written for that too. For the car, print our free corgi and train coloring pages.
A bedtime story after seeing SantaRally Takes the Train is a five-minute rhyming picture book about a corgi’s first ride on a California train, hand-painted in watercolor. $16.99 on Amazon, ages 0 to 8.
Buy on AmazonKeep the Christmas magic going: track Rally the corgi on Christmas Eve, print free Christmas coloring pages, learn how to say Merry Christmas in 100+ languages, find train museums to visit with kids, or browse Christmas events in every Oregon city.
Milwaukie Christmas events for kids: questions parents ask
What are the best Christmas events for kids in Milwaukie this year?
Rally Takes the Train has confirmed 2 Christmas events for kids in Milwaukie for 2026, both from the City of Milwaukie: the Umbrella Parade and Tree Lighting on December 5 and Winter Solstice and Christmas Ships on December 19.
When is the Milwaukie Umbrella Parade in 2026?
Saturday, December 5, 2026. The parade leaves the South Downtown Plaza at 4:30 pm, and contest entrants must arrive by 4:15 pm.
Can kids win prizes at the Umbrella Parade?
Yes. Each category, including Most Creative, Most Festive and Most Milwaukie, has prizes for children and adults, and there is a prize for the best decorated bicycle.
When can you see the Christmas Ships in Milwaukie?
The city calendar lists Winter Solstice and Christmas Ships for Saturday, December 19, 2026, from 4:30 to 7:30 pm at Milwaukie Bay Park, with a bonfire and food for sale.
Who do I contact about Milwaukie holiday events?
The City of Milwaukie events team at events@milwaukieoregon.gov.
Are there Christmas train rides for kids in Oregon?
Yes. Santa trains and holiday train rides have their own guide: Rally Takes the Train’s Oregon Christmas train rides page.
How do you confirm these events?
We list an event only after we find this season’s date on the host’s own website or an official city or tourism calendar. We last checked Milwaukie on November 11, 2026. Rally is also contacting each organizer to confirm details like parking, restrooms and bad-weather plans.
Event names belong to their hosts. Rally Takes the Train is a family picture book and is not affiliated with, sponsored by or endorsed by any host listed here. Confirm dates, times and prices on each host’s own site before you go.