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.
July 2025
July 8, 2025 ~ Highland Rodeo Club Association Barrel Racing Series ~ 4907 Lagoon Rd, Highland Exhibitions start at 6:00 p.m. ~ Jackpot at 7:00 p.m. Flyer
July 5, 2025 ~ 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 Flyer
July 10, 2025 ~ Highland Park Improvements ~ Music in the Park Live Music by Jesse Bauman
July 13, 2025 ~ Open Mic @ Spurgeon Vineyards & Winery 16008 Pine Tree Rd, Highland WI 53543 Contact Spurgeon Vineyards & Winery for more information at (608) 929-7692 Flyer
July 17-19, 2025 ~ 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 19, 2025 ~ 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. Flyer
July 19-20, 2025 ~ 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 Flyer
July 2025 ~ 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
July 24, 2025 ~ Highland Park Improvements ~ Music in the Park Live Music by Abbey Lane
August 2025
August 2, 2025 ~ 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 Flyer
August 7, 2025 ~ Highland Park Improvements ~ Music in the Park Live Music Big Cat Eddie
August 9, 2025 ~ 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. Flyer
August 17, 2025 ~ Open Mic @ Spurgeon Vineyards & Winery 16008 Pine Tree Rd, Highland WI 53543 Contact Spurgeon Vineyards & Winery for more information at (608) 929-7692 Flyer
August 2025 ~ Highland Lion's Club Movie Night & Stuff the Bus Highland Village Park, 755 Park St, Highland WI Free showing of _________________ at dusk ~ free concessions will be provided Will be collecting items for Stuff the Bus for the Highland School District Bring items to donate and be entered into door prize drawing 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 20, 2025 ~ Highland Park Improvements ~ Music in the Park Live Music Doug Wayne
August 23, 2025 ~ 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 $20.00 (12 and under free) ~ No carry-ins For more information call (608) 732-6953 or email [email protected]
August 30-31, 2025 ~ 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 Flyer
September 2025
September 6, 2025 ~ 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 Flyer
September 9, 2025 ~ Highland Rodeo Club Association Barrel Racing Series ~ 4907 Lagoon Rd, Highland Exhibitions start at 6:00 p.m. ~ Jackpot at 7:00 p.m. Flyer
September 2025 ~ Highland Volunteer Fire Dept Fall Festival Highland Village Park, 755 Park St
September 2025 ~ Highland Schools Homecoming Thursday - Spirit Night at Highland High School Gym at 7:00 p.m. Friday - 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. Weston/Wonewoc Center 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 20-21, 2025 ~ 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 Flyer
September 14, 2025 ~ Open Mic @ Spurgeon Vineyards & Winery 16008 Pine Tree Rd, Highland WI 53543 Contact Spurgeon Vineyards & Winery for more information at (608) 929-7692 Flyer
September 2025 ~ Ss. Anthony & Philip Oktoberfest Celebration Contact Ss. Anthony & Philip Church for more information at (608) 929-7490
September 2025 ~ Open Book Highland Village Hall 530 Main St, Highland WI 53543 2024 OPEN BOOK Contact the Village Office if you have any questions at (608) 929-7781
September 2025 ~ Board of Review at 6:00 p.m. Highland Village Hall 530 Main St, Highland WI 53543 2024 NOTICE OF BOARD OF REVIEW Contact the Village Office if you have any questions at (608) 929-7781
October 2025
October 4, 2025 ~ 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 Flyer
October 10-12, 2025 ~ Harvest Festival ~ Spurgeon Vineyards & Winery 16008 Pine Tree Rd, Highland WI 53543 Contact Spurgeon Vineyards & Winery for more information at (608) 929-7692 Flyer
October 18, 2025 ~ 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. Flyer
October 2025 ~ 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 26, 2025 ~ Open Mic @ Spurgeon Vineyards & Winery 16008 Pine Tree Rd, Highland WI 53543 Contact Spurgeon Vineyards & Winery for more information at (608) 929-7692 Flyer
October 2025 ~ Halloween Trick-or-Treating
October 2025 ~ Halloween in Highland Trunk or Treat
November 2025
November 1, 2025 ~ 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 Flyer
November 9, 2025 ~ Open Mic @ Spurgeon Vineyards & Winery 16008 Pine Tree Rd, Highland WI 53543 Contact Spurgeon Vineyards & Winery for more information at (608) 929-7692 Flyer
November 11, 2025 ~ Veterans Day Program Highland Elementary Gym Starts at 2:00 p.m.
November 22-23, 2025 ~ 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 27, 2025 ~ 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 2025
December 2025 ~ Holidays in Highland
December 2025 ~ Highland School Holiday 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 2025 ~ Highland Elementary School Holiday Concert Highland Elementary School Gym 1030 Cardinal Drive, Highland Dress Rehearsal at 2:00 p.m. or Evening Performance at 7:00 p.m. Contact the School Office for more info at (608) 929-4525
January 2026
January 2026 ~ Highland Lion's Club Fisheree Blackhawk Lake Recreation Area, 2025 County Road BH Gates open at 5:00 a.m. ~ FREE PARK ADMISSION Contact Sheri Esser (608) 553-1340 or Mike Spink (608) 574-4258 for more info
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 ~ Spring Primary Highland Village Hall, 530 Main St, Highland, WI Polls open from 7:00 a.m. to 8:00 p.m. Contact Becky Fredericks for more information at (608) 929-7781
March 2026 ~ Highland School Pops Concert Concert ~ 7:00 p.m. Contact Highland Schools for more information (608) 929-4525
March 2026 ~ Knights of Columbus Pancake Breakfast More details to follow when shared with the village
March 2026 ~ Highland Drama Club Musical
March 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
April 2026
April 7, 2026 ~ Spring Election Highland Village Hall, 530 Main St, Highland, WI Polls open from 7:00 a.m. to 8:00 p.m. Contact Becky Fredericks for more information at (608) 929-7781
April 2026 ~ Highland Park Improvements Annual Color Run/Walk April 2026 ~ Village Wide Garage Sales Please check the Highland, WI Garage Sale Facebook page for further information https://www.facebook.com/groups/246843571225627
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]
May 2026
May 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 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 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 ~ Open Mic @ Spurgeon Vineyards & Winery 16008 Pine Tree Rd, Highland WI 53543 Contact Spurgeon Vineyards & Winery for more information at (608) 929-7692
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 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 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 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 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
June 2026
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 ~ 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 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.
June 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 2026 ~ Open Mic @ Spurgeon Vineyards & Winery 16008 Pine Tree Rd, Highland WI 53543 Contact Spurgeon Vineyards & Winery for more information at (608) 929-7692
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