Over about one week in mid-October, Stillwater's calendar changes direction. Harvest Fest fills Lowell Park and the Riverwalk on October 10 and 11. Four days later, on October 15, the U.S. Coast Guard's regular lift schedule for the Stillwater Lift Bridge ends. After that, the dated events on the town's calendar happen on weeknights and on Main Street, and that holds through December 20. If you live here, the pumpkin weekend is the last stop of the river season. After it, the calendar runs on storefronts and Thursday nights.
Saturday Belongs to the Scale, Sunday to the River
Stillwater Harvest Fest is free and is held the second weekend of October. The organizers call it one of the largest giant pumpkin festivals in the Midwest. They also say it has been the top giant pumpkin weigh-off in the world several times, measured by the combined weight of the ten heaviest pumpkins, and that it produced a world record pumpkin in 2010. The festival is produced by Summer Tuesday, Inc., a nonprofit.
The two days are planned very differently. Saturday is built around the scale and the food. Sunday ends at the water and under a crane. Here are the times from the 2026 printable schedule:
| Event | Saturday, Oct. 10 | Sunday, Oct. 11 |
|---|---|---|
| Food truck and vendor market | 10 a.m.–7 p.m. | 10 a.m.–6 p.m. |
| Giant pumpkin weigh-off | 10 a.m.–3 p.m. | — |
| Ferris wheel | 10 a.m.–8 p.m. | 10 a.m.–6 p.m. |
| Beer garden, Bayport American Legion | 10 a.m.–8 p.m. | 10 a.m.–6 p.m. |
| Chili cook-off tasting | 1–4 p.m. | — |
| Pie eating contest | 2:30 p.m. | — |
| Kids costume parade | — | 11:30 a.m., line up at stage |
| Battle to Paddle | — | Noon |
| Pumpkin regatta | — | 2:30 p.m. |
| Curio Dance "Thriller" | — | 5 p.m. |
| Giant pumpkin drop | — | 5:30 p.m. |
| Light Warrior Fire Dance | — | 7 p.m. |
The regatta takes place on the St. Croix River. The pumpkin drop is from a 100-foot crane. Two times are listed differently depending on where you look. The festival homepage lists drops at 5:30 p.m. on both Saturday and Sunday, but the printable schedule shows only Sunday's. The FAQ gives the regatta start as about 2:15 p.m., while the schedule says 2:30. If either event is the reason you're going, check with the organizers that morning.
The live music stage is sponsored by Andersen Windows. On Saturday, Lars Carlson & the Secondhand Hipsters open at 10 a.m. and Free & Easy Band closes from 6 to 8 p.m. On Sunday, Marv & Kaat play at 10 a.m., PK Mayo at 12:30 p.m., and Joe Cruz & Scenic Roots at 3 p.m. Joseph's Restaurant, Find My Fidget, and St. Croix Auto sponsor the pie eating contest. The sponsor list is mostly local names. Discover Stillwater and St. Croix Automotive are listed at the Great Pumpkin level, and Leo's Grill, Acadian Building, Candyland, and Water Street Inn are organizing sponsors.
Four Downtown Lots Become the Festival
Downtown parking shrinks most on this weekend, because the festival takes over some of the lots. Lots 4, 5, 9, and 11 are inside the event area and won't be available for parking. Shuttles run from Stillwater Middle School and the Bayport Legion to the U.S. Bank stop at 2nd and Chestnut, about every 15 to 20 minutes:
- Saturday: 10 a.m. to 9 p.m.
- Sunday: 10 a.m. to 7:30 p.m.
Sunday's last shuttle leaves an hour and a half after the Ferris wheel stops and two hours after the pumpkin drop. That leaves enough time to watch the 7 p.m. fire dance and still ride back to your car. We didn't find any published street-closure details for 2026, so plan for heavier traffic than normal along the riverfront blocks.
October 15, the Bridge Goes Call-Ahead
The festival's last weekend comes right before the river season ends. The Coast Guard sets the Lift Bridge's regular schedule, which runs from May 15 to October 15 each year. During the season MnDOT staffs the bridge from 8 a.m. to midnight. This year's schedule started on Wednesday, May 6. MnDOT usually keeps the lift schedule going until late October when weather and staffing allow.
From late October to early May, the bridge goes up only with 24 hours' notice, requested through MnDOT's dispatch line at 651-234-7110. If you have a boat still in the water, Harvest Fest weekend is close to your last chance to pass under on the regular schedule without calling ahead.
The bridge has construction work this fall as well. MnDOT's 2026 metro construction list includes replacing the electrical cables on the Stillwater Lift Bridge pedestrian bridge, scheduled for September through December 2026. MnDOT's materials don't give any specific closure dates for walkers, so check the bridge's status before planning a walk across to Wisconsin.
Where the Evenings Go Next
With the riverfront season over, downtown evenings move indoors and onto Thursday through Saturday nights. Stillwater Zephyr Theatre and Stillwater Trolley Co. run the Haunted History Trolley Tour out of River Siren Brewing at 225 Main St. N. The tour runs on these dates:
- Friday and Saturday, October 9–10
- Thursday through Saturday, October 15–17
- Thursday through Saturday, October 22–24
- Thursday and Friday, October 29–30
The first two tour nights fall on the Friday and Saturday of Harvest Fest weekend. The rest run on Thursday through Saturday evenings for the remainder of October, so the downtown calendar has something on several weeknights after the riverfront crowds leave.
The weekend events through December mostly move indoors as well. RSG Development has three craft and vendor shows on the schedule:
- the Fall Craft & Vendor Show on Saturday, October 17, 10 a.m. to 4 p.m., at Stillwater Area High School, 5701 Stillwater Blvd. N.
- a show at the Stillwater Armory, 350 Maryknoll Drive N., on Saturday, November 7, 10 a.m. to 4 p.m.
- the Holiday Craft & Gift Show at Oak Glen Golf Course, 1599 McKusick Road, on December 12 from 10 a.m. to 4 p.m. and December 13 from 10 a.m. to 2 p.m.
Main Street's Storefronts Are Changing This Season
As events move from the river to Main Street, it matters more what's open there, and several storefronts are changing. The Tilted Tiki at 324 S. Main St. announced in July that it was closing permanently. Dave Dahl, Paul Barber, and Dave Eichten plan to open Dave Dahl's Tornado Room Bar & Grill in the same space. In July the Pioneer Press reported an expected September opening. As of early October, the restaurant's own site still says it isn't open yet and that the date will be announced once it's set. The menu preview describes a weather-themed bar and grill with an F5 roast beef sandwich, broasted chicken, a Hail Mary Bloody Mary, and rotating local beer and wine. The site also lists planned hours that run until midnight Sunday through Thursday and 1 a.m. on Fridays and Saturdays. If it opens with those hours, Main Street gets a late-night option just as the river season ends.
Sara's Bake Shop has moved into Brine's Market & Deli. The bakery's last day at its old shop was set for July 11, and the plan was to offer its full lineup inside Brine's starting July 14. Up the hill, the city's Fall 2026 newsletter expected the Chick-fil-A at 2001 Washington Ave. to open in October. The same newsletter said the rebuilt Amoco at 103 Main St. N. would open soon, with site work wrapping up this fall.
Outdoor Routes Once the Riverfront Quiets Down
The newsletter also says the city will build a trail connection from Sunrise Park to Stillwater Boulevard, also known as County Road 5, this fall. On Brown's Creek State Trail, the DNR plows the eastern section between Laurel Street and Manning Avenue in winter. The western section toward Duluth Junction isn't maintained. That leaves the Laurel-to-Manning stretch as the cleared trail route after the snow comes.
The Calendar From Here to December 20
Community Thread's Hometown for the Holidays fills Main Street in late November and December. Proceeds benefit the group's Holiday Hope program. The 2026 schedule has four weekends and three Luminary Thursdays:
- Small Business Weekend, November 27–29: Black/Plaid Friday and Small Business Saturday specials.
- Twinkle Weekend, December 3–6: a Christmas tree lighting on Saturday evening, followed by fireworks over the river.
- Candy Town Weekend, December 10–13: the gingerbread house contest is on Saturday.
- Paws & Claus Weekend, December 17–20: a pet parade and costume contest.
Luminary Thursdays fall on December 3, 10, and 17, the first night of each of the last three weekends. Luminaries line Main Street, and downtown businesses may run special offers. Community Thread says its full event schedule is coming soon, so exact times and locations for each activity haven't been posted yet. The fireworks on Twinkle Weekend are the only event over the river on the holiday schedule.
If you're looking at downtown Stillwater for your next home, whether near the river or within walking distance of Main Street, Farida Karundeng can show you which blocks are closest to the festival footprint and how parking and access work during big event weekends. You can see more on our Stillwater neighborhood page, or reach out when you're ready. Let's Connect.
