After the Last Market Saturday: How Lake Oswego Fills Its Weekends From Halloween to the Holiday Trolley

The Lake Oswego Farmers' Market's last regular Saturday is October 31, 2026. It runs 8:30 a.m. to 1:30 p.m. at Millennium Plaza Park, as it has on Saturdays since May 9, with July 4 the only skipped date. Through the season, Saturday mornings downtown worked without a plan. You walked over when it suited you, bought what looked good and left.

The six weeks after that work differently. The market comes back only twice, and the city's paid fall and holiday extras run on reservations. Wagon rides leave on the hour. Santa visits come in 15-minute slots. The holiday trolley has fixed departures and requires a reservation. Going by the Parks & Recreation Fall 2026 Activity Guide, a November or December weekend in Lake Oswego goes better if you've booked it in advance.

October 31 ends the walk-up season twice

This year is the market's 25th season. When it opened in May, market manager Shelley Burgess told the Lake Oswego Review that the plan was for 220 vendors, among them Wild Geese Farm, which grows at Luscher Farm. She also said new vendors would bring olive oil, wine, baked goods, toys and tea. The October 31 market is the last chance this year to shop that full lineup on a regular Saturday.

The city's Halloween event starts after the market packs up. Monster Mash runs from 2 to 5 p.m. at Christ Church Parish, 1060 Chandler Road. The city lists trick-or-treating, crafts and music, with free bags for the first 400 guests. The activity guide describes trick-or-treat streets with sweets, toys and trinkets at every station, and welcomes children ages 0 to 12.

The free bags cap out at 400, and that's the only limit on the day. Both October 31 events are walk-up.

The next morning, the market moves to Lake Grove

The market team runs one more open-air event the day after Halloween. The First Sunday Market in Lake Grove sets up on Hallmark Drive from 11 a.m. to 2:30 p.m., and the November 1 theme is Pet-a-Palooza. The city's page lists a pet parade and costume contest, pet portraits, and vendors selling treats and gear for pets. Regular produce, makers, food and live music are there too, and the listing says "Leashes encouraged, tails welcome!"

The First Sunday Market page lists only two dates for the rest of the year. The other was October 4, a Back to School Block Party. That leaves November 1 as the last Lake Grove date on the 2026 schedule. The activity guide adds SNAP matching up to $20 and Farm Fresh Kids activities at First Sunday markets. If last weekend's Halloween costume still fits the dog, it can go to the parade.

November 21 is the first weekend you have to plan ahead for

Market vendors come back once more for the Reunion Farmers' Market at Millennium Plaza Park on Saturday, November 21, from 9 a.m. to 2 p.m. The city calls it a fall-harvest shopping event with returning vendors, live music and local artisans. The activity guide pitches it as "Fresh from local farms to your Thanksgiving table!" Live music runs from 10:30 a.m. to 12:30 p.m., with SNAP matching up to $20 and Farm Fresh Kids activities.

The market itself is walk-up, but the horse-drawn wagon rides that go with it are mostly booked. They leave from Millennium Plaza Park for a tour of downtown that takes about 20 minutes. Reserved departures are on the hour at 9, 10, 11 a.m. and noon. First-come tickets for the half-hour rides are sold onsite. Tickets cost $15 for adults and $10 for youth ages 0 to 12, through loparks.org or by phone at 503-675-2549.

The listing has four reserved departures. Families who want a set time and don't want to wait for a half-hour ride will need to book before the Saturday before Thanksgiving.

The holiday calendar, by how you get in

The Tree Lighting is the last big walk-up event. After it, the city's December events are paid and timed. Here is how each one handles entry, according to the city's listings:

The Tree Lighting Festival is the big open event of the season. It runs from 3 to 7 p.m. on the day after Thanksgiving, and the City of Lake Oswego and the Lake Oswego Chamber of Commerce host it together. The city lists a holiday marketplace, winery row, Santa, reindeer and performances. The Millennium tree is lit at 5:30 p.m. The guide adds letters to Santa, sweet treats and photos with Santa.

The December 5 event at Christ Church Parish has two sessions. From 10 a.m. to 2 p.m., sensory-friendly Santa visits give children ages 0 to 12 a calm, quiet place to meet Santa. The guide says they're designed for children with sensory sensitivities or special needs. From 2 to 4 p.m., the event offers Santa photos with pets. Both sessions need pre-registration for 15-minute slots, at $15 per slot.

The trolley weekend fills by departure time

The Tinseltown Trolley has the tightest schedule of the season. It runs Friday through Sunday, December 11 to 13, from the Willamette Shore Trolley station at 311 N State Street. Each ride takes about 45 minutes on a decorated trolley, with holiday lights, games, treats and carols, and a visit from "a special guest from the North Pole" when it gets back to the station. Tickets cost $20 for children 12 and under and $25 for adults, and reservations are required.

These are the departure times listed in the guide:

1. Friday: 1:30, 2:45, 4 and 5:15 p.m.
2. Saturday: 11 a.m., 12:15, 1:30, 2:45, 4, 5:15 and 6:30 p.m.
3. Sunday: departures start at 11 a.m. and 12:15 p.m., with more listed in the guide

Saturday has seven departures, the most of the three days, and the latest one.

What's open on State Street between bookings

Timed slots leave gaps in the day. Booking a 45-minute trolley ride puts you on North State Street with time to spare before or after, and there's a new spot a short walk up the street.

The Oswegian is a public house at 456 N State St., in the former Gemini Bar space. In August, owner Sean Casey told What Now Portland he was aiming for a late-August or early-September opening. He described beer, a full bar and a food menu, and said he planned to book live bands. The Oswegian's website listed live music at 9 p.m. on October 9 and 10. It also lists $1 Taco Tuesdays after 5 p.m. and weekday happy hour, Monday through Friday, 5 to 7 p.m. The online menu wasn't posted at the time of writing, so check the latest before you go.

A longtime downtown name is in a holding pattern. The Lake Oswego Ice Creamery and Restaurant is at 37 A Ave. On September 3, the Lake Oswego Review reported that a sign there described it as temporarily "closed for renovations." We haven't found a later update on its plans.

A riverfront route without a ticket

The city's Willamette River Greenway Trail project is filling a gap between Foothills Park, Roehr Park and George Rogers Park. The finished trail will be a continuous 2.25-mile multi-use path along the Willamette River, with walking and biking connections to downtown from neighborhoods south of George Rogers Park and Oswego Creek.

The city's project page estimates completion and opening in Fall 2026 and says the schedule is subject to change. City Council authorized a contract with Daybreak Construction in May, and the groundbreaking was held at George Rogers Park on July 15. The estimated cost is $1,760,000. The groundbreaking is the latest update posted, and the page doesn't announce an opening date. Once it opens, it will connect George Rogers Park to downtown, close to where the wagon and trolley rides depart, and you won't need a ticket to use it.

If your fall and holiday plans include getting your home ready for the spring market, Green Buck Real Estate can give you a clear read on what it's worth before the calendar fills up. Request a free home valuation, and we'll work around your trolley time.