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.
June 2024
June 1, 2024 Sips and Songs Saturday @ Spurgeon Vineyards & Winery
Enjoy free Live Music from 1:00 p.m. thru 4:00 p.m.
Bring your own lawn chair if you like!
16008 Pine Tree Rd, Highland WI 53543
Contact Spurgeon Vineyards & Winery for more information at 608.929.7692
June 6, 2024 Grab A Cone Trailer
Parked in the Village of Highland Parking Lot ~ 2:00 p.m. to 7:00 p.m.
June 8-9, 2024 Highland Rodeo Club
Little Britches Rodeo ~ Highland Rodeo Grounds ~ 4907 Lagoon Rd, Highland
June 9, 2024 American Legion & VFW Chix BBQ
Highland Village Park, 755 Park St
Serving Chicken BBQ Dinner at Noon ~ Approx. 550 dinners
For home deliveries call 608.341.7665
Come out and support your local veterans!!!
June 9, 2024 Pickleball Tournament
Highland Village Park, 755 Park St
June 22-23, 2024 Bring ON the Bacon & Cheese Days ~ Spurgeon Vineyards & Winery
Wine ~ Food ~ Live Music ~ Vendor Fair
Live music from 1:00 p.m. to 4:00 p.m. both days
16008 Pine Tree Rd, Highland WI 53543
Contact Spurgeon Vineyards & Winery for more information at 608.929.7692
July 2024
July 6, 2024 Sips and Songs Saturday @ Spurgeon Vineyards & Winery
Enjoy free Live Music from 1:00 p.m. thru 4:00 p.m.
Bring your own lawn chair if you like!
16008 Pine Tree Rd, Highland WI 53543
Contact Spurgeon Vineyards & Winery for more information at 608.929.7692
July 11, 2024 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 18-20, 2024 Our Town Celebration
Sponsored by the Highland Lion's Club ~ All activities subject to change
2024 Our Town Event Poster
Contact Mike Spink @ 608.574.4258 or Sheri Esser @ 608.553.1340 with questions or concerns
July 20-21, 2024 Way COOL Wine Weekend ~ Spurgeon Vineyards & Winery
Wine ~ Food ~ Live Music ~ Vendor Fair
Live music from 1:00 p.m. to 4:00 p.m. both days
16008 Pine Tree Rd, Highland WI 53543
Contact Spurgeon Vineyards & Winery for more information at 608.929.7692
July 25, 2024 Highland Park Improvements ~ Music in the Park
Live Music by Doug Wayne
August 2024
August 3, 2024 Sips and Songs Saturday @ Spurgeon Vineyards & Winery
Enjoy free Live Music from 1:00 p.m. thru 4:00 p.m.
Bring your own lawn chair if you like!
16008 Pine Tree Rd, Highland WI 53543
Contact Spurgeon Vineyards & Winery for more information at 608.929.7692
August 8, 2024 Highland Park Improvements ~ Music in the Park
Live Music by Bryce Bird
August 17-18, 2024 WURST Wine Weekend EVER ~ Spurgeon Vineyards & Winery
Wine ~ Food ~ Live Music ~ Vendor Fair
Live music from 1:00 p.m. to 4:00 p.m. both days
16008 Pine Tree Rd, Highland WI 53543
Contact Spurgeon Vineyards & Winery for more information at 608.929.7692
August 2024 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 24, 2024 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 29, 2024 Highland Park Improvements ~ Music in the Park
Live Music by Jesse Bauman
September 2024
September 7, 2024 Sips and Songs Saturday @ Spurgeon Vineyards & Winery
Enjoy free Live Music from 1:00 p.m. thru 4:00 p.m.
Bring your own lawn chair if you like!
16008 Pine Tree Rd, Highland WI 53543
Contact Spurgeon Vineyards & Winery for more information at 608.929.7692
September 13-15, 2024 Highland Firemen's Labor Day Picnic
Highland Village Park, 755 Park St
Chicken BBQ on Sunday serving starts at 11:00 a.m
October 2024
October 5, 2024 Sips and Songs Saturday @ Spurgeon Vineyards & Winery
Enjoy free Live Music from 1:00 p.m. thru 4:00 p.m.
Bring your own lawn chair if you like!
16008 Pine Tree Rd, Highland WI 53543
Contact Spurgeon Vineyards & Winery for more information at 608.929.7692
October 2024 Ss. Anthony & Philip Oktoberfest Celebration
Drive Thru or Dine In - 10:00 a.m. to 1:00 p.m.
SSAP Famous German Meal
Contact Ss. Anthony & Philip Church for more information at 608.929.7490
October 2024 Highland Schools Homecoming
Friday - Spirit Night (skits, coronation & yell) at 7:00 p.m.
Saturday - Parade at 11:00 a.m.
Saturday - Football game at 2:00 p.m. vs. Hillsboro
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
October 12-13, 2024 Harvest Festival ~ Spurgeon Vineyards & Winery
Wine ~ Food ~ Live Music ~ Vendor Fair
Live music from 1:00 p.m. to 4:00 p.m. both days
16008 Pine Tree Rd, Highland WI 53543
Contact Spurgeon Vineyards & Winery for more information at 608.929.7692
October 18, 19, 25 & 26, 2024 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
Trick or Treating on Sunday afternoon
November 2024
November 2, 2024 Sips and Songs Saturday @ Spurgeon Vineyards & Winery
Enjoy free Live Music from 1:00 p.m. thru 4:00 p.m.
Bring your own lawn chair if you like!
16008 Pine Tree Rd, Highland WI 53543
Contact Spurgeon Vineyards & Winery for more information at 608.929.7692
November 2024 Veterans Day Program
Highland Elementary Gym
Starts at 2:00 p.m.
November 23-24, 2024 Christmas Open House ~ Spurgeon Vineyards & Winery
Wine ~ Food ~ Live Music ~ Vendor Fair
Live music from 1:00 p.m. to 4:00 p.m. both days
16008 Pine Tree Rd, Highland WI 53543
Contact Spurgeon Vineyards & Winery for more information at 608.929.7692
November 2024 Highland Lions Club Free Community Thanksgiving Dinner
Highland Volunteer Fire Department
11:00 a.m. to 2:00 p.m.
709 Dodgeville St, Highland WI 53543
RSVP appreciated but not required ~ call 608.929.7413 and leave message
December 2024
December 2024 Holidays in Highland
8th Annual Craft & Vendor Fair 8:30 a.m. to 1:00 p.m.
Highland Community Schools
1030 Cardinal Drive, Highland, WI
Light Parade at 6:00 p.m.
Parade Entry Form ~ holidayslightparadeentry23
Follow their Facebook page at Holidays in Highland for more information
December 2024 Highland School Holiday Concert
Middle & High School Band & Choir
Highland Elementary School Gym
1030 Cardinal Drive, Highland
7:00 p.m.
Contact the School office for more info at 608.929.4525
December 2024 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 2025
January 2025 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 2025
February 2025 Highland Ambulance Service Valentine's Breakfast
Highland School District Commons, 1030 Cardinal Drive
February 2025 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.
By donating at this blood drive, you are helping one or more graduating seniors earn a scholarship.
February 2025 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
February 2025 Highland Summer Rec Taste of Summer
Highland Park Concessions, 755 Park St, Highland, WI
Serving from 5:00 p.m. to 7:00 p.m. or until sold out
Famous Park Burger with bag of chips, cookie and water - $10
For in town delivery call 608.553.0599
All proceeds will go towards the purchase of needed equipment.
March 2025
March 2025 Highland School Pop's Concert and Pasta Supper
Supper ~ 4:00 p.m. to 6:45 p.m.
Concert ~ 7:00 p.m.
Contact Highland Schools for more information 608.929.4525
March 2025 Ss. Anthony & Philip's St. Pat's Dinner
Ss. Anthony & Philip Church, 726 Main St
Serving from 10:00 a.m. to 1:00 p.m.
Dine in or carry out
Call 608.929.7490 for more information
April 2025
April 2025 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 2025 Village Wide Garage Sales
Please check the Highland, WI Garage Sale Facebook page for further information
https://www.facebook.com/groups/246843571225627
April 2025 Prescription Drug Take-Back Day
Village of Highland Police Department
530 Main St, Highland WI 53543
TIME CHANGE ~ 6:00 p.m. to 8:00 p.m.
For more information call Officer Swinehart at 608.574.4615
or email him at [email protected]
MAY 2025
May 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
May 2025 Highland School Prom
Highland School, 1030 Cardinal Drive, Highland
Dance from 8:00 p.m. to 11:30 p.m.
Contact the School Office for more info at 608.929.4525
May 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
May 2025 Highland Community Schools Creativity Expo & K-12 Art Fair
Highland School District, 1030 Cardinal Dr
Contact Highland Schools for more information 608.929.4525
May 2025 Middle School and High School Spring Concert
Highland Elementary Gym, 1030 Cardinal Drive
Concert at 7:00 p.m.
Contact Highland Schools for more information 608.929.4525
May 2025 Highland Elementary Spring Concert
Highland Elementary School Gym, 1030 Cardinal Drive, Highland
Concert at 7:00 p.m.
Contact the School Office for more info at 608.929.4525
May 24, 2025 High School Graduation
Highland School Distrcit, 1030 Cardinal Drive
Commencement starts at 11:00 a.m.
Contact Highland Schools for more information 608.929.4525
May 2025 Great Wine & Chocolate Weekend ~ Spurgeon Vineyards & Winery
Wine ~ Food ~ Live Music ~ Vendor Fair
Live music from 1:00 p.m. to 4:00 p.m. both days
16008 Pine Tree Rd, Highland WI 53543
Contact Spurgeon Vineyards & Winery for more information at 608.929.7692
May 2025 8th Grade Graduation
Highland School District, 1030 Cardinal Drive
Contact Highland Schools for more information 608.929.4525