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.
MAY 2025
May 3, 2025 ~ 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 3, 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
May 8-9 2025 ~ Highland Community Schools Creativity Expo
Highland School District, 1030 Cardinal Drive
Contact Highland Schools for more information 608.929.4525
May 9, 2025 ~ Highland Fire Department Steak Feed
Highland Fire Station, 709 Main Street, Highland
May 13, 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.
May 15, 2025 ~ 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 18, 2025 ~ Open Mic @ Spurgeon Vineyards & Winery
16008 Pine Tree Rd, Highland WI 53543
Contact Spurgeon Vineyards & Winery for more information at 608.929.7692
May 19, 2025 ~ 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 19, 2025 ~ 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 20, 2025 ~ 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 24, 2025 ~ 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 24-25, 2025 ~ Great Wine & Chocolate Weekend ~ Spurgeon Vineyards & Winery
16008 Pine Tree Rd, Highland WI 53543
Contact Spurgeon Vineyards & Winery for more information at 608.929.7692
May 30, 2025 ~ 8th Grade Graduation
Highland School District, 1030 Cardinal Drive
Contact Highland Schools for more information 608.929.4525
June 2025
June 6, 2025 ~ 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 7, 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
June 7-8, 2025 ~ Highland Rodeo Club Association
Little Britches of Wisconsin Rodeo ~ 4907 Lagoon Rd, Highland
Start time 9:00 a.m. each day
June 8, 2025 ~ American Legion & VFW Chix BBQ
Highland Village Park, 755 Park St
Come out and support your local veterans!!!
June 10, 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.
June 21-22, 2025 ~ 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 29, 2025 ~ Open Mic @ Spurgeon Vineyards & Winery
16008 Pine Tree Rd, Highland WI 53543
Contact Spurgeon Vineyards & Winery for more information at 608.929.7692
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.
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
July 10, 2025 ~ Highland Park Improvements ~ Music in the Park
Live Music TBD
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
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.
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
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 TBD
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
August 7, 2025 ~ Highland Park Improvements ~ Music in the Park
Live Music TBD
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.
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
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 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 24, 2025 ~ Highland Park Improvements ~ Music in the Park
Live Music TBD
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
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
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.
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
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
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
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
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.
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
October 2025 ~ Halloween Trick-or-Treating
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
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
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
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 ~ Highland Ambulance Service Valentine's Breakfast
Highland EMS Valentine Breakfast 2025
Serving from 8:00 a.m. to Noon
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
Register or request an absentee ballot at https://myvote.wi.gov/en-us/
March 2026
March 2026 ~ Highland Summer Rec Taste of Summer
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
Register or request an absentee ballot at https://myvote.wi.gov/en-us/
Type E Notice ~ Absentee Voting
Type D Notice ~ Polling Place Location & Hours
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]