City-Wide Rummage Sales
Pipestone City-Wide Rummage Sales are held annually in late April or Early May. In 2026, these dates are April 30 - May 2, 2026. Please contact the Pipestone County Star & Free Star at 507-825-3333 for advertising information.
2026 Chamber Car Cruise-Ins
- Dates Yet To Be Announced
Enjoy music and relaxation as you stroll amongst classic cars! Pipestone's Chamber Car Cruise-Ins feature show cars and hobby vehicles from local and regional enthusiasts. The events are FREE entry for everyone! Food is available for purchase. Prize drawings are held for all registered vehicles! Click HERE for the Community Calendar.
The Pipestone Cruizers CAR SHOW at Water Tower Festival is held next to the Pipestone County Courthouse on Saturday, June 27, 2026 from 10:00 am to 3:00 pm (Registration is at 9:00 am; Awards at 2:00 pm). There is a fee to register. The first 100 registered vehicles receive a FREE Car Show Dash Plate. Awards! Prizes! Prize Drawings!
2026 Water Tower Festival
Thursday through Sunday, June 25-28, 2026
Annually, Pipestone celebrates the Water Tower Festival surrounding the last Saturday in June. Residents and visitors turn out en masse for this favorite community get together! The festival commemorates the restoration of the city's historic concrete water tower as a community landmark. The festival kicks off with a city-wide Water Tower Festival Medallion Hunt on Monday, June 22, 2026 where the lucky winner receives bragging rights, the carved pipestone medallion, and a prize! Other festival events include an awesome parade, kids' activities, live music, entertainment, street dance, community dinners, musical theater performance "The Wizard of Oz" at the Pipestone Performing Arts Center, kids' inflatables, huge car show, arts & crafts fair, delicious foods, community church service, and class/family reunions! No Festival entrance fee and most individual events are FREE to attend. (2026 Parade Theme: "Minnesota Icons"). Click HERE for Details & Current Schedule.
Future Water Tower Festival Parade Dates:
- 2027: Saturday, June 26
- 2028: Saturday, June 24
2026 Pipestone Crazy Days
Dates Yet to Be Announced (typically late July)
Shop 'til you drop while enjoying CrAzY shopping deals at local businesses all around town and more!
2026 Pipestone County Fair
Wednesday through Saturday, August 5-8, 2026
Our old-fashioned county fair is annually a top event in the region! Bring your kids to the Children's Barn to see and pet baby farm animals! Watch piglets being born! Annual Grandstand Entertainment regularly includes live music, NPTA Truck & Tractor Pull, and more! Bring your appetite for Steak Night, Pork Chop Night, BBQ Ribs Night, the famous Dar's Pizza Night, and local food stands including the Jaycees Dugout for adult beverages! 4-H, FFA, and open class exhibitors share various exhibits including livestock, arts & crafts, photography, produce, and flowers with the public. The youngest residents and young at heart can't wait for the Midway featuring rides for all ages, carnival games, and classic fair food! Plus, lots of daily fun from magicians to music to face painting to bingo and more! And, don't forget the Annual Pipestone Area Chamber's Youth Ribbon Auction and Ranch Rodeo on the final day of the fair. Family Fun for EVERYONE! FREE Admission to the Pipestone County Fair. Midway rides & games and some Grandstand events have individual fees. Click HERE for more information.
9th Annual Kids' Fishing Derby at The Pond and Community Meal
Date Yet to Be Announced (held annually in July or August)
One of our most popular community-wide end-of-summer celebrations will be back again in 2026. Kids ages 15 and under dip their lines in the ol' Quarry Pond while competing for trophies and prizes given for First Fish Caught, Shortest Fish, Longest Fish, Lightest Fish, and Heaviest Fish. Plus, door prizes too! Exact start time and details to come, however the fishing derby will be held in the early evening. Prior to the fishing derby, everyone is invited to come share a FREE community meal at the beautiful Hiawatha Pageant Park!
Hosted and Sponsored by the Pipestone Area Chamber of Commerce, Pipestone Kiwanis Club, & City of Pipestone with the assistance and sponsorship of many community sponsors.
12th Annual Downtown Trunk or Treat
Thursday, October 29, 2026, 4:30 pm - 6:00 pm (on Main Street)
The Pipestone Area Chamber of Commerce invites you to Historic Downtown Pipestone for the FREE 12th Annual Trunk or Treat & Downtown Candy Walk on Thursday, October 29st, from 4:30 pm to 6:00 pm. With 800-1,000 kids plus their families and other residents attending annually, this community celebration for our area’s youth is truly a Pipestone Area favorite! Three blocks of Main Street in our Historic Downtown are closed to traffic to allow for safe, family-friendly fun, candy, and music! If you are a local business, church, club, school, team, or non-profit organization that would like to participate by decorating a trunk, please contact the Chamber at 825-3316 as pre-registration is required. Click HERE for more information.
7th Annual Lights at The Lodge
Saturday, November TBA, 2026 through January 1, 2027
Experience the beauty of winter at the Hiawatha Pageant Park nightly! Drive or walk through viewing of lighted Christmas trees will be available nightly, November TBA, 2026 through January 1, 2027 after the opening Lighting and Luminaria Walk on November TBA. A number of Holiday Photo Op stations are available throughout the Park.
This event is organized by the City of Pipestone’s Hiawatha Pageant Park Commission and made possible by all of our community members who adopt the trees.
11th Annual Shop Pipestone
Date & Details Yet to Be Announced (typically late November)
Make a BIG impact in your local community. Support Local!
Santa Claus Comes to Town & Santa’s Workshop!
Date & Details Yet to Be Announced
Even Santa thinks Pipestone is America's #CoolestSmallTown!
Join Us for this FUN, FREE event for the whole family. Meet Santa, drop off your Letter, take a photo with the Big Guy, and enjoy several Make-and-Take activities for kids. The event sponsored by the Pipestone Area Chamber of Commerce and Pipestone County 4-H Ambassadors.
