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.
September 2023
September 1-3, 2023 Highland Firemen's Labor Day Picnic
Highland Village Park, 755 Park St
Chicken BBQ on Sunday serving starts at 11:00 a.m.
September 2, 2023 Live Music @ Spurgeon Vineyards & Winery
16008 Pine Tree Rd, Highland WI 53543
Contact Spurgeon Vineyards & Winery for more information at (608) 929-7692
September 23, 2023 Backroad Summer Party at Bootlegger's
545 Main St, Highland WI 53543
Meat Paddles & 50/50 Raffles
Starting at 4:00 p.m.
Drawing at 8:00 p.m. ~ 1st: $1,000 ~ 2nd: $500 ~ 3rd: $250
Live Music by High Mileage Band from 7:00 p.m. to 11:00 p.m. ~ $5 cover
Meal: pulled pork or turkey & dressing sandwich, chips & baked beans ~$7.00
Contact Bootleggers at (608) 929-4814 with any questions
October 2023
October 1, 2023 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 6 & 7, 2023 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 7 & 8, 2023 Harvest Festival - Spurgeon Vineyards & Winery
FREE live music ~ bring your own lawn chairs
Hot food available for purchase
FREE wine tasting ~ FREE winery tours
10:00 a.m. to 5:00 p.m.
16008 Pine Tree Rd, Highland WI 53543
Contact Spurgeon Vineyards & Winery for more information at 608.929.7692
October 20, 21, 27 & 28, 2023 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 29, 2023 Halloween Trick-or Treating
Highland EMS and Fire will collaborate with other local groups to sponsor Trick or Treating
Starts at 1:00 p.m. for some fun events at the Highland Historical Society gymnasium
Please keep an eye on the Highland Ambulance Service - Highland Trick or Treating Facebook page for more details
If you are a local organization and would like to help with this event contact Tammy Benish or message on the Facebook page
October 31, 2023 Halloween in Highland Trunk or Treat
Highland Village Park, 755 Park St, Highland
Trunk or Treat ~ 5:15 p.m. to 6:00 p.m. ~ $5.00/child
Movie ~ 6:15 p.m.
Popcorn and hot chocolate will be available for purchase
All proceeds will go towards the Highland Park Improvement Project
November 2023
November 10, 2023 Veterans Day Program
Highland Elementary Gym
Starts at 2:00 p.m.
November 18 & 19, 2023 Christmas Open House - Spurgeon Vineyards & Winery
Super Sale on Select Wines ~ Free Wine Tasting ~ Free Local Product Tasting
10:00 a.m. to 5:00 p.m.
16008 Pine Tree Rd, Highland WI 53543
Contact Spurgeon Vineyards & Winery for more information at (608) 929-7692
December 2023
December 2, 2023 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
More information to follow
Follow their Facebook page at Holidays in Highland for more information
December 12, 2023 Highland School Holiday Concert
Middle School & 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 21, 2023 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 2024
January 2024 Highland Lion's Club Fisheree
Blackhawk Lake Recreation Area, 2025 County Road BH
Gates Open at 5:00 a.m. FREE PARK ADMISSION
For more information please contact
Sheri Esser (608) 553-1340 or Mike Spink (608) 574-4258
February 2024
February 2024 Ss. Anthony & Philip's Church Super Bowl Pre-Game Party
Ss. Anthony & Philip Church Lower Level, 726 Main St
Call (608) 929-7490 for more information
February 2024 Highland Ambulance Service Valentine's Breakfast
Highland School District Commons, 1030 Cardinal Drive
February 2024 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 2024 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.
Famous Park Burger with bag of chips, cookie and water - $10 (Buy 4 meals, get 1 free)
For in town delivery call 608.553.0599
All proceeds will go towards the purchase of needed equipment and a new shed.
February 2024 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.
March 2024
March 2024 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.
March 2024 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 929-4525
March 2024 Highland Boosters & Parent Club Fundraiser
Highland Historical Society Gym, 526 Isabell St
Dinner & Silent Auction 5:00-8:00 p.m.
Iowa County Cattleman's Steak Sandwich Dinner - $13
Hot Dog Dinner - $5
Live Auction at 8:00 p.m.
Auction Contacts:
Molly Leibfried: [email protected] ~ 608.574.5765
Kirsten Rusch: [email protected] ~ 608.341.8922
April 2024
April 2, 2024 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
2023-4-4 SPRING ELECTION SAMPLE BALLOT
April 2024 Open Book 2:30 p.m. to 4:30 p.m.
Highland Village Hall
530 Main St, Highland WI 53543
Contact the Village Office if you have any questions at (608) 929-7781
April 2024 Prescription Drug Take-Back Day
Village of Highland Police Department
530 Main St, Highland WI 53543
10:00 a.m. to 2:00 p.m.
For more information check out the Law Enforcement Section
or call Officer Swinehart at (608) 574-4615
or email him at [email protected]
April 2024 Board of Review at 6:00 p.m.
Highland Village Hall
530 Main St, Highland WI 53543
Contact the Village Office if you have any questions at (608) 929-7781
MAY 2024
May 2024 Village Wide Garage Sales
May 2024 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 2024 Highland Community Schools Creativity Expo & K-12 Art Fair
Highland School District, 1030 Cardinal Dr
For more information contact Highland School at (608) 929-4525
May 2024 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 2024 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 25, 2024 High School Graduation
Highland School Distrcit, 1030 Cardinal Drive
Commencement starts at 1:30p.m.
Contact Highland Schools for more information (608) 929-4525
May 2024 The Great Wine & Chocolate Trail - Spurgeon Vineyards & Winery
Pairing luscious chocolates with our Fine Wine
10:00 a.m. to 5:00 p.m.
$20 per person ~ includes live music
16008 Pine Tree Rd, Highland WI 53543
Contact Spurgeon Vineyards & Winery for more information at (608) 929-7692
June 2024
June 2024 8th Grade Graduation
Highland School Distrcit, 1030 Cardinal Drive
Contact Highland Schools for more information (608) 929-4525
June 2024 Highland Tractor Pullers Spring Farm Pull
Highland Rodeo Grounds, 4907 Lagoon Rd, Highland WI
Starts at 5:00 p.m.
For more information call 608.732.6953 or email [email protected]
June 2024 Live Music @ Spurgeon Vineyards & Winery
16008 Pine Tree Rd, Highland WI 53543
Contact Spurgeon Vineyards & Winery for more information at (608) 929-7692
June 9, 2024 American Legion & VFW Chix BBQ
Highland Village Park, 755 Park St
Serving Chicken BBQ Dinner
Refreshment Stand
Come out and support your local veterans!!!
June 2024 Bring on the Bacon & Cheese Days - Spurgeon Vineyards & Winery
Pairing Prime bacon treats and Artisan Cheese with our Fine Wine
10:00 a.m. to 5:00 p.m.
$20 per person ~ includes live music
16008 Pine Tree Rd, Highland WI 53543
Contact Spurgeon Vineyards & Winery for more information at (608) 929-7692
July 2024
July 2024 Highland Rodeo Club
Little Britches Rodeo
Highland Rodeo Grounds, 4907 Lagoon Rd
Start time is 10:00 a.m. both days
Contact Sarah Winkler for more information @ 608.341.7183 or
[email protected]
July 2024 Live Music @ Spurgeon Vineyards & Winery
16008 Pine Tree Rd, Highland WI 53543
Contact Spurgeon Vineyards & Winery for more information at (608) 929-7692
July 2024 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 2024 Way Cool Wine Days - Spurgeon Vineyards & Winery
Making Mixers and Slushies with our Fine Wine and served with food
10:00 a.m. to 5:00 p.m.
$20 per person ~ includes live music
16008 Pine Tree Rd, Highland WI 53543
Contact Spurgeon Vineyards & Winery for more information at 608.929.7692
August 2024
August 2024 Christ Lutheran Church Outdoor Christian Concert
Highland Village Park, 755 Park St, Highland
Freewill Offering starting at 6:30p.m.
Music by Ken Drury & Ben Schmidtke Jr
Familiar and Original Gospel Music
Sponsored by Christ Lutheran Church/Ladies Aid
In case of rain, concert will be held at the church ~ 303 Main St, Highland
August 2024 Live Music @ Spurgeon Vineyards & Winery
16008 Pine Tree Rd, Highland WI 53543
Contact Spurgeon Vineyards & Winery for more information at 608.929.7692
August 2024 Iowa County Cancer Coalition Fundraiser Event
Ss. Anthony & Philip Church, 726 Main St, Highland WI
Food & Beverages ~ 4-7 p.m.
Pork meal catered by Red Zone ~ kids meal available
Beverages sold bBeverages sold by Highland Fire Department
Children Activities ~ 4-7 p.m.
Memorial Luminaries & Ribbons for sale ~ 4-7 p.m.
Silent Auction ~ 4-6:30 p.m.
Live Auction with Larry Springer & On Point Auction ~ 6 p.m.
Proceeds stay in Iowa County directly helping cancer patients
To contact Iowa County Cancer Coalition ~ 608.623.2095 ~ www.iowacountycancercoalition.org
August 2024 Wurst Wine Weekend EVER - Spurgeon Vineyards & Winery
Pairing Bratwurst and German Food with our Fine Wine
10:00 a.m. to 5:00 p.m.
$20 per person ~ includes live music
16008 Pine Tree Rd, Highland WI 53543
Contact Spurgeon Vineyards & Winery for more information @ 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 2024 Highland Nationals by Highland Tractor Pullers & Badger State Tractor Pullers
Highland Rodeo Grounds, 4907 Lagoon Rd, Highland WI
Starts at 6:00 p.m.
Admission $10.00 (8 and under free) ~ No carry-ins
For more information call 608.732.6953 or email [email protected]