Downtown Lee's Summit's Holiday Season Runs Through Green Street

The Wednesday and Saturday farmers market at Green Street ends its 2026 season on Saturday, Oct. 31. That date doesn't mark a slow stretch for downtown Lee's Summit. The Halloween parade's costume contest, the Mayor's Tree Lighting, the Holiday Mart and a December jazz fundraiser are all scheduled at the same 17,140-square-foot hall at 209 SE Green St. The idea is the same one the market tested all year. When people have a warm, dry place to start, they stay downtown longer.

What the first full season showed

The 2026 market was the first full season in the building. Before Green Street opened in August 2025, the market ran in a parking lot at Douglas and Second streets. The new space is climate-controlled, with large windows and public restrooms.

The numbers from the move are large. In an April 2026 preview, Jenny Gale, assistant director of Downtown Lee's Summit Main Street and manager of the Green Street Market, told the Lee's Summit Journal that market crowds grew by close to 300% after the 2025 move. Saturdays typically drew more than 3,000 people, and vendors were "selling out by 10:30 or 11." The old lot had room for about 40 vendors. The 2026 plan called for around 70 sellers on Saturdays and about 35 on Wednesdays.

The number that matters most for the holiday calendar is about time. Gale told the Journal that after the move, the average customer spent twice as long at the market or in the downtown shopping district. "They are picnicking, they're going to lunch and they're shopping at all the businesses," she said. Karin Velez of Wolf Creek Family Farm described the same thing in that story. Shoppers can now spend several hours, grab a coffee or something to eat, and take their time.

The fall and winter events follow that pattern. The biggest downtown events start at Green Street, and the rest of the calendar fills Main Street, the history museum and the Amtrak station a few blocks away.

October's last market Saturdays, with something else attached

The final two weeks of the regular season each pair a market morning with a second event.

Saturday, Oct. 17. The Downtown Lee's Summit Haunted & Historic Spaces Tour runs 6 to 8 p.m. and starts at Green Street. Downtown Lee's Summit Main Street presents it with Summit Theatre Group and the Lee's Summit History Museum. Groups leave in six staggered starts between 6 and 7:40 p.m. The same night, Team Cocktail hosts Team Cocktail After Dark, a spooky shopping event from 7 to 10 p.m. One evening covers a guided walk through old downtown buildings followed by an open shop down the street.

Saturday, Oct. 31. Halloween falls on the last day of the 2026 market season, and the two schedules overlap. The market is open 8 a.m. to noon. The Boos, Barks & Badges Halloween Parade begins with a costume contest at Green Street at 9:30 a.m. At 10 a.m. the parade leaves City Hall for Howard Station Park, followed by games and trick-or-treating at participating businesses until noon. Downtown Lee's Summit Main Street hosts it. On one morning you can shop the final market produce, enter the costume contest and walk the route, all inside a few downtown blocks.

Lee's Summit Parks and Recreation runs two Halloween events at Legacy Park that week if you want something else. The free Trunk or Treat is Thursday, Oct. 22, at Legacy Park Amphitheater. The city's listing gives no start time yet. The Floating Pumpkin Patch is Saturday, Oct. 24, from 10:30 a.m. to 12:30 p.m. at the J. Thomas Lovell Jr. Community Center.

November: two market days a week become four Saturdays a season

The hall is still in use after the regular season ends. Weekly shopping is replaced by the Lee's Summit Farmers Market Holiday Mart presented by Thermal King Windows. It runs four Saturdays at Green Street, 10 a.m. to 2 p.m., with handcrafted gifts, baked goods, locally raised meats and seasonal produce. Downtown Lee's Summit Main Street organizes it. As of its September listing, vendors are "to be announced soon."

The Holiday Mart's later hours fit with the rest of the calendar. The regular market closed at noon, while the Holiday Mart runs until 2 p.m. On three of its four dates, that leaves an hour before Selfies with Santa starts at the history museum.

Here is the full downtown run from Halloween through mid-December, as currently posted.

The Veterans Day Parade: America 250 is organized by Jack Ray VFW Post 5789 and its Auxiliary. It steps off at SE Main and SE 3rd on Saturday, Nov. 7. That's the second day of the Holiday Open House, when downtown shops feature holiday shopping and decor.

The Mayor's Tree Lighting is presented by Security Bank of Kansas City with Downtown Lee's Summit Main Street and the City. It's the biggest single night at Green Street this season, with live music, holiday vendors, activities and Santa. Gates open at 5 p.m. and the program starts at 6.

The Saturdays where everything overlaps

Three Saturdays carry most of the season: Nov. 28, Dec. 5 and Dec. 19. On each one, the Holiday Mart's morning hours sit next to an afternoon event a few blocks away.

Nov. 28 is also Small Business Saturday. Downtown Lee's Summit Main Street is promoting tote bags and a scratch-to-win gift card offer at downtown shops. Selfies with Santa at the Lee's Summit History Museum starts that afternoon at 3 p.m. and is free.

Dec. 5 has the most going on. Using only the posted times, a full Saturday downtown could look like this:

1. Holiday Mart at Green Street opens at 10 a.m., for gifts and baked goods.
2. All Aboard with Santa on the Missouri River Runner is due at the Lee's Summit Amtrak station, 217 SW Main St., at 1:03 p.m. A train ticket is all you need. There's no separate event ticket.
3. The Holiday Mart wraps up at 2 p.m.
4. Selfies with Santa runs at the History Museum from 3 to 5 p.m.

If Saturday doesn't work, the Santa train also stops in Lee's Summit at 9:16 a.m. on Sunday, Dec. 6.

Dec. 19 is the final Holiday Mart and the last Selfies with Santa afternoon. Four days earlier, on Tuesday, Dec. 15, the Lee's Summit Jazz Orchestra holds its Winter Wonderland Fundraiser at Green Street from 6 to 7:30 p.m.

A new stop on Main since the summer

There's one more reason to walk past Green Street this season. Well Read Bookstore, owned by Anna Buser, opened in the former KD's Books storefront at 241 SE Main St. Link 2 Lee's Summit reported that the shop had opened by the week of its Aug. 28 grand-opening event. That means the Holiday Open House on Nov. 6–7 and Small Business Saturday on Nov. 28 will be its first holiday shopping weekends on Main Street.

That's the kind of foot traffic Gale described in the spring. Shoppers leave the market, walk around downtown and support the brick-and-mortar businesses, which she told the Journal is also one of Downtown Lee's Summit Main Street's goals. The market used to stop when the weather turned. This year, Green Street is booked through Dec. 19.

Some details are still unconfirmed: Holiday Mart vendors, and hours for the Open House, Small Business Saturday and the Legacy Park Trunk or Treat. Check downtownls.org and the city's parks page the week of each event.

If one of these Saturdays has you thinking about what it would be like to live within walking distance of downtown, Sherry Lynn & Co knows the streets around Green Street. We're happy to walk you through what's for sale near Main Street. Schedule a consultation whenever you're ready.