We try to enter events as we know them and we try to keep them as current as possible. However, sometimes events change and we miss that. So please check with the contact person to confirm the event is still scheduled.
January 2026
January 2026 ~ Highland Lion's Club Fisheree Lions Club Fisheree 2026 Blackhawk Lake Recreation Area ~ 2025 County Road BH, Highland WI Gates open at 5:00 a.m. ~ FREE PARK ADMISSION Highland Historical Society ~ 526 Isabell St, Highland WI Doors open 10:00 a.m.
February 2026
February 2026 ~ Highland Community Blood Drive St. Anthony & Philip Parish Center, 723 Main Street 12:00 p.m. to 5:00 p.m. For an appointment call 1-800-RED CROSS (1-800-733-2767) or visit redcrossblood.org Bring a friend and help save lives together.
February 2026 ~ Highland Ambulance Service Valentine Breakfast Serving from 8:00 a.m. to Noon
February 28, 2026 ~ Knights of Columbus Pork Chop Dinner St. Anthony & Philip Parish Center, 723 Main Street Serving open from 4:00 p.m. to 7:00 p.m. Contact Dennis Richgels for in Village deliveries at 608.341.7665
March 9, 2026 ~ Highland School Pops Concert Concert ~ 7:00 p.m. Contact Highland Schools for more information 608.929.4525
March 15, 2026 ~ Ss. Anthony & Philip's St. Pat's Dinner Ss. Anthony & Philip Church, 726 Main St Dine in or carry out Call 608.929.7490 for more information
March 29, 2026 ~ Highland Park Improvements Breakfast w/the Bunny & Easter Egg Hunt
April 2026
April 4, 2026 ~ Sips N' Songs Saturday @ Spurgeon Vineyards & Winery 16008 Pine Tree Rd, Highland WI 53543 Contact Spurgeon Vineyards & Winery for more information at 608.929.7692
April 19, 2026 ~ Open Mic @ Spurgeon Vineyards & Winery 16008 Pine Tree Rd, Highland WI 53543 Contact Spurgeon Vineyards & Winery for more information at 608.929.7692
April 2026 ~ Prescription Drug Take-Back Day Village of Highland Police Department For more information call Officer Swinehart at 608.574.4615 or email him at [email protected]
April 2026 ~ Vilalge of Highland Open Book Highland Village Hall ~ 530 Main St Hours _________________________ Contact the Village Office if you have any questions at 608.929.7781
May 2026
May 2, 2026 ~ Highland School Prom Highland School, 1030 Cardinal Drive, Highland Dance from 8:00 p.m. to 11:30 p.m. ~ Grand March at 8:30 p.m. Contact the School Office for more info at 608.929.4525
May 2, 2026 ~ Sips N' Songs Saturday @ Spurgeon Vineyards & Winery 16008 Pine Tree Rd, Highland WI 53543 Contact Spurgeon Vineyards & Winery for more information at 608.929.7692
May 7-8, 2026 ~ Highland Community Schools Creativity Expo Highland School District, 1030 Cardinal Drive Contact Highland Schools for more information 608.929.4525
May 10, 2026 ~ Open Mic @ Spurgeon Vineyards & Winery 16008 Pine Tree Rd, Highland WI 53543 Contact Spurgeon Vineyards & Winery for more information at 608.929.7692
May 18, 2026 ~ Middle School and High School Spring Concert Highland Elementary School Gym, 1030 Cardinal Drive Concert at 7:00 p.m. Contact Highland Schools for more information 608.929.4525
May 21, 2026 ~ Highland Elementary Spring Concert Highland Elementary School Gym, 1030 Cardinal Drive Dress Rehearsal at 2:00 p.m. ~ Concert at 6:00 p.m. Contact the School Office for more info at 608.929.4525
May 23, 2026 ~ High School Graduation Highland School District, 1030 Cardinal Drive Commencement starts at 11:00 a.m. Contact Highland Schools for more information 608.929.4525
May 23-24, 2026 ~ Great Wine & Chocolate Weekend ~ Spurgeon Vineyards & Winery 16008 Pine Tree Rd, Highland WI 53543 Contact Spurgeon Vineyards & Winery for more information at 608.929.4525
May 29, 2026 ~ 8th Grade Graduation Highland School District, 1030 Cardinal Drive Contact Highland Schools for more information 608.929.4525
May 2026 ~ Highland Fire Department Steak Feed Highland Fire Station, 709 Main Street, Highland
May 2026 ~ Highland Rodeo Club Association Barrel Racing Series ~ 4907 Lagoon Rd, Highland Exhibitions start at 6:00 p.m. ~ Jackpot at 7:00 p.m.
May 2026 ~ Highland Community Schools Art Fair/Book Fair Book Fair ~ Buy One, Get One Free Highland School District, 1030 Cardinal Drive Contact Highland Schools for more information 608.929.4525
May 2026 ~ Highland Community Schools Art Fair/Book Fair Book Fair ~ Buy One, Get One Free Highland School District, 1030 Cardinal Drive Contact Highland Schools for more information 608.929.4525
November 2026 ~ Village of Highland Board of Review Highland Village Hall, 530 Main St Board of Review will start at _____ p.m. Contact the Village Office if you have any questions at 608.929.7781
June 2026
June 6, 2026 ~ Highland Park Improvements Annual Color Run/Walk
June 6, 2026 ~ Sips N' Songs Saturday @ Spurgeon Vineyards & Winery 16008 Pine Tree Rd, Highland WI 53543 Contact Spurgeon Vineyards & Winery for more information at 608.929.7692
June 13-14, 2026 ~ Bring ON the Bacon & Cheese Days ~ Spurgeon Vineyards & Winery 16008 Pine Tree Rd, Highland WI 53543 Contact Spurgeon Vineyards & Winery for more information at 608.929.7692
June 28, 2026 ~ Open Mic @ Spurgeon Vineyards & Winery 16008 Pine Tree Rd, Highland WI 53543 Contact Spurgeon Vineyards & Winery for more information at 608.929.7692
June 2026 ~ Highland Rodeo Club Association Open Barrel Racing ~ 4907 Lagoon Rd, Highland Exhibitions start at 6:00 p.m. ~ Jackpot at 7:00 p.m.
June 2026 ~ Highland Rodeo Club Association Little Britches of Wisconsin Rodeo ~ 4907 Lagoon Rd, Highland Start time 9:00 a.m. each day
June 2026 ~ American Legion & VFW Chix BBQ Highland Village Park, 755 Park St Come out and support your local veterans!!!
June 2026 ~ Highland Rodeo Club Association Barrel Racing Series ~ 4907 Lagoon Rd, Highland Exhibitions start at 6:00 p.m. ~ Jackpot at 7:00 p.m.
July 2026
July 4, 2026 ~ Sips N' Songs Saturday @ Spurgeon Vineyards & Winery 16008 Pine Tree Rd, Highland WI 53543 Contact Spurgeon Vineyards & Winery for more information at 608.929.7692
July 12, 2026 ~ Open Mic @ Spurgeon Vineyards & Winery 16008 Pine Tree Rd, Highland WI 53543 Contact Spurgeon Vineyards & Winery for more information at 608.929.7692
July 18-19, 2026 ~ Way COOL Wine Weekend ~ Spurgeon Vineyards & Winery 16008 Pine Tree Rd, Highland WI 53543 Contact Spurgeon Vineyards & Winery for more information at 608.929.7692
July 22, 2026 ~ Highland Park Improvements ~ Music in the Park Live Music by Abbey Lane
July 2026 ~ Highland Rodeo Club Association Barrel Racing Series ~ 4907 Lagoon Rd, Highland Exhibitions start at 6:00 p.m. ~ Jackpot at 7:00 p.m.
July 2026 ~ Our Town Celebration Sponsored by the Highland Lion's Club ~ All activities subject to change Contact Mike Spink @ 608.574.4258 or Sheri Esser @ 608.553.1340 with questions or concerns
July 2026 ~ Highland Rodeo Club Association Barrel Racing Series & Roping ~ 4907 Lagoon Rd, Highland Exhibitions start at 6:00 p.m. ~ Jackpot at 7:00 p.m. Will not rope before 1:00 p.m.
July 2026 ~ Christ Lutheran Church Outdoor Christian Concert Highland Village Park, 755 Park St, Highland Freewill Offering starting at 6:00p.m. Sponsored by Christ Lutheran Church/Ladies Aid
August 2026
August 1, 2026 ~ Sips N' Songs Saturday @ Spurgeon Vineyards & Winery 16008 Pine Tree Rd, Highland WI 53543 Contact Spurgeon Vineyards & Winery for more information at 608.929.7692
August 5, 2026 ~ Highland Park Improvements ~ Music in the Park Live Music Big Cat Eddie
August 9, 2026 ~ Open Mic @ Spurgeon Vineyards & Winery 16008 Pine Tree Rd, Highland WI 53543 Contact Spurgeon Vineyards & Winery for more information at 608.929.7692
August 19, 2026 ~ Highland Park Improvements ~ Music in the Park Live Music by Logan Bollant
August 29-30, 2026 ~ WURST Wine Weekend EVER ~ Spurgeon Vineyards & Winery 16008 Pine Tree Rd, Highland WI 53543 Contact Spurgeon Vineyards & Winery for more information at 608.929.7692
August 2026 ~ Highland Rodeo Club Association Barrel Racing Series & Roping ~ 4907 Lagoon Rd, Highland Exhibitions start at 6:00 p.m. ~ Jackpot at 7:00 p.m. Will not rope before 1:00 p.m.
August 2026 ~ Highland Lion's Club Movie Night & Stuff the Bus Highland Village Park, 755 Park St, Highland WI Free showing of _______________ at dusk ~ free concessions at 7:00 p.m. Will be collecting items for Stuff the Bus for the Highland School District Bring items to donate ~ markers, crayons (24 ct), color pencils, pencil boxes, highlighters, scotch tape, black sharpies, dry erase markers, kleenex, glue, 1/2" & 1" binders, notebooks and all other common school supplies. Items needed ~ markers, 24ct crayons, colored pencils, pencil boxes, highlighters, scotch tape, black sharpies, dry erase markers, kleenex, glue, 1' & 1 1/2" binders, notebooks
August 2026 ~ Highland Booster Club Booster Bash Dinner ~ 5:00 p.m. to 7:00 p.m. ~ burgers, brats, hot dogs, chips, beans, drinks Silent Auction ~ 5:00 p.m. to 7:30 p.m. Live Auction ~ 7:00 p.m.
August 2026 ~ Highland Nationals by Highland Tractor Pullers & Badger State Tractor Pullers Highland Rodeo Grounds, 4907 Lagoon Rd, Highland WI Local classes starts at 2:00 p.m. ~ Badger State Tractor Pull starts at 6:00 p.m. Admission __________ (12 and under free) ~ No carry-ins For more information call 608.732.6953 or email [email protected]
September 2026
September 2, 2026 ~ Highland Park Improvements ~ Music in the Park Live Music by Jesse Bauman
September 5, 2026 ~ Sips N' Songs Saturday @ Spurgeon Vineyards & Winery 16008 Pine Tree Rd, Highland WI 53543 Contact Spurgeon Vineyards & Winery for more information at 608.929.7692
September 13, 2026 ~ Open Mic @ Spurgeon Vineyards & Winery 16008 Pine Tree Rd, Highland WI 53543 Contact Spurgeon Vineyards & Winery for more information at 608.929.7692
September 16, 2026 ~ Highland Park Improvements ~ Music in the Park Live Music by Doug Wayne
September 19-20, 2026 ~ Art in the Valley @ Spurgeon Vineyards & Winery 16008 Pine Tree Rd, Highland WI 53543 Contact Spurgeon Vineyards & Winery for more information at 608.929.7692
September 26, 2026 ~ Highland Schools Homecoming Spirit Night at Highland High School Gym at 7:00 p.m. Hall of Fame Banquet at Highland High School Gym at 7:00 p.m. Saturday ~ Parade at 11:00 a.m. Saturday ~ Football game at 2:00 p.m. vs. ____________________ Saturday ~ Homecoming Dance from 8:00 p.m. to 11:00 p.m. with Grand March at 8:30 p.m. Contact Highland School District for more information at 608.929.4525
September 2026 ~ Highland Rodeo Club Association Barrel Racing Series ~ 4907 Lagoon Rd, Highland Exhibitions start at 6:00 p.m. ~ Jackpot at 7:00 p.m.
September 2026 ~ Highland Volunteer Fire Dept Fall Festival Highland Village Park, 755 Park St
October 2026
October 3, 2026 ~ Sips N' Songs Saturday @ Spurgeon Vineyards & Winery 16008 Pine Tree Rd, Highland WI 53543 Contact Spurgeon Vineyards & Winery for more information at 608.929.7692
October 9-11, 2026 ~ Harvest Festival ~ Spurgeon Vineyards & Winery 16008 Pine Tree Rd, Highland WI 53543 Contact Spurgeon Vineyards & Winery for more information at 608.929.7692
October 18, 2026 ~ Open Mic @ Spurgeon Vineyards & Winery 16008 Pine Tree Rd, Highland WI 53543 Contact Spurgeon Vineyards & Winery for more information at 608.929.7692
October 31, 2026 ~ Halloween Blast ~ Spurgeon Vineyards & Winery 16008 Pine Tree Rd, Highland WI 53543 Contact Spurgeon Vineyards & Winery for more information at 608.929.7692
October 2026 ~ Ss. Anthony & Philip Oktoberfest Celebration Contact Ss. Anthony & Philip Church for more information at 608.929.7490
October 2026 ~ Highland Rodeo Club Association Barrel Racing Series & Roping ~ 4907 Lagoon Rd, Highland Exhibitions start at 6:00 p.m. ~ Jackpot at 7:00 p.m. Will not rope before 1:00 p.m.
October 2026 ~ Highland Community Haunted Hayride 5718 Hines Rd, Highland WI ~ 608.929.7650 First wagon will leave at dark, last tickets sold at 10:00 p.m. Cancellations will be posted on Facebook & local radio, including 99.3 (WDMP) and 97.7 (WGLR). Find us on Facebook for last minute updates - Highland Haunted Hayride: Haunting for a Cause
October 2026 ~ Halloween Trick-or-Treating
November 2026
November 7, 2026 ~ Sips N' Songs Saturday @ Spurgeon Vineyards & Winery 16008 Pine Tree Rd, Highland WI 53543 Contact Spurgeon Vineyards & Winery for more information at 608.929.7692
November 15, 2026 ~ Open Mic @ Spurgeon Vineyards & Winery 16008 Pine Tree Rd, Highland WI 53543 Contact Spurgeon Vineyards & Winery for more information at 608.929.7692
November 2026 ~ Veterans Day Program Highland Elementary Gym Starts at 2:00 p.m.
November 20-21, 2026 ~ Christmas Open House ~ Spurgeon Vineyards & Winery 16008 Pine Tree Rd, Highland WI 53543 Contact Spurgeon Vineyards & Winery for more information at (608) 929-7692 Flyer
November 2026 ~ Highland Lions Club Community Thanksgiving Dinner Highland Volunteer Fire Department 11:00 a.m. to 2:00 p.m. 709 Dodgeville St, Highland WI 53543709 Dodgeville St, Highland WI 53543 Dine in, carryouts and delivery available Donations welcome, contact (608) 929-7413
December 2026
December 2026 ~ Holidays in Highland
December 2026 ~ Highland School Christmas Concert Middle & High School Band & Choir Highland Elementary School Gym 1030 Cardinal Drive, Highland Performance at 7:00 p.m. Contact the School office for more info at (608) 929-4525
December 2026 ~ Highland Elementary School Christmas Concert Highland Elementary School Gym 1030 Cardinal Drive, Highland Dress Rehearsal at 2:00 p.m. or Evening Performance at 6:00 p.m. Contact the School Office for more info at (608) 929-4525
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