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.
August 2021
August 14 & 15, 2021 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. - Reservation required - $15 per person
16008 Pine Tree Rd, Highland WI 53543
Contact Spurgeon Vineyards & Winery for more information @ 608.929.7692
August 28, 2021 8th Annual Highland Truck and Tractor Pull
Highland Rodeo Grounds, 4907 Lagoon Rd, Highland WI
Starts at 2:00 p.m.
For more information contact Dave Gates @ 608.732.6953
September 2021
September 3-5 2021 Highland Firemen's Labor Day Picnic
Highland Village Park, 755 Park St
Concession Stand Open All Weekend
Music all Weekend
Paintball Games
Chicken BBQ on Sunday serving starts at 11:00 a.m.
Bean Bag Tournament - Sunday starting at 2:00 p.m.
Raffle Drawing - Sunday at 3:00 p.m.
Contact Brian Brown for more information at 608.341.8358
September 25 & 26, 2021 Harvest Festival - Spurgeon Vineyards & Winery
Live Music - Bring your own lawn chair
Food available and wine tasting
10:00 a.m. to 5:00 p.m.
16008 Pine Tree Rd, Highland WI 53543
Contact Spurgeon Vineyards & Winery for more information @ 608.929.7692
October 2021
October 2021 Highland School Athletic Hall of Fame Banquet
Ss. Anthony & Philip Church, 726 Main St, Highland
Starts at 7:00 p.m.
Contact Highland School for more info at 608.929.4525
October 9, 2021 Highland High School Homecoming
October 8-9, 2021 Highland School Homecoming
Friday Skit Night
Saturday Parade
Saturday Football Game
Saturday Homecoming Dance
Contact Highland School for more info at 608.929.4525
October 2021 Ss Anthony & Philip Church Oktoberfest
Ss Anthony & Philip Church, 726 Main St, Highland
Serving from 10:00 a.m. to 1:00 p.m. - $12.00
BBQ Pork, German potato salad, sauerkraut, mashed potatoes and gravy, carrots, roll and dessert
This year they will be having a silent auction, view items at www.ssanthonyphilip.com
Bids taken by calling 608.929.7701 or email Mark Hebgen [email protected]
Call 608.929.7490 for more information
October 2021 Highland Rodeo Club Open Fun Horse Show
Highland Rodeo Grounds, 4907 Lagoon Rd
Registration at 12:00 p.m. - Start at 1:00 p.m.
Check it out on Facebook at Highland Rodeo Club
Contact Sarah Winkler for more information (608) 341-7183 or [email protected]
October 22, 23, 29 & 30, 2021 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.
Cost is $5.00/person
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
Knights of Columbus 1909 Pancake Breakfast
St. Thomas Church Lower Level
104 Park St, Montfort WI
Serving from 8:00 a.m. to Noon
Pancakes, scrambled eggs, sausage, rolls, coffee and milk
Prescription Drug Take-Back Day
Village of Highland Police Department
530 Main St, Highland WI
11:00 a.m. to 2:00 p.m.
Contact Daniel Swinehart for more information at (608) 574-4615
October 2021 Halloween Trick-or Treating
3:00 p.m. to 6:00 p.m. - please turn on your porch light if you want to participate
October 30 & 31, 2021 Halloween Party - Spurgeon Vineyards & Winery
Pairing Halloween candy with our Fine Wines
Ghoulish recipes and more!
10:00 a.m. to 5:00 p.m. - Reservation required - $15 per person
16008 Pine Tree Rd, Highland WI 53543
Contact Spurgeon Vineyards & Winery for more information at (608) 929-7692
November 2021
November 2021 Knights of Columbus Steak Supper
Highland Fire Station, 709 Dodgeville St, Highland WI
Serving from 5:00 p.m. to 7:30 p.m.
November 2021 Christ Lutheran Church Soup Supper
Serving 4:30 p.m. to 7:00 p.m.
303 Main Street, Highland WI
Chili, Cheesy Potato-Ham and Chicken Noodle
Adults - $9.00, Children - $4.00, Under 5 free; Carryouts available
November 2021 VFW & American Legion Veterans Sunday Brunch
Serving 8:30 a.m. to 12:30 p.m.
The Red Zone, 360 Main St, Highland WI
Adults - $12.00, Children - $5.00, Under 6 Free
Help us continue to serve out Community, Veterans, Military Families, Students and others
November 2021 Veterans Day Program
Highland Elementary Gym
Starts at 2:00 p.m.
November 20 & 21, 2021 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 2021
December 2021 Holidays in Highland Wagon Ride Caroling
Leaving from church parking lot (top of Main St)
December 2021 Holidays in Highland Home Outdoor Lighting & Decorating Contest
December 4, 2021 5th Annual Holidays in Highland
Activity List, Details and Schedule coming soon
December 2021 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 2021 Highland Elementary School Holiday Concert
Highland Elementary School Gym
1030 Cardinal Drive, Highland
7:00 p.m.
Contact the School Office for more info at (608) 929-4525
January 2022
January 2022 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 infomration please contact
Sheri Esser (608) 553-1340 or Mike Spink (608) 574-4258
February 2022
February 2022 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 2022 Highland Ambulance Service Valentine's Breakfast
Highland School District Commons, 1030 Cardinal Drive
February 15, 2022 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 2022 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.orgBring a friend and help save lives together.
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 2022
March 2022 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 2022 Ss. Anthony & Philip's St. Pat's Dinner
Ss. Anthony & Philip Church, 726 Main St
Call (608) 929-7490 for more information
April 2022
April 5, 2022 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 2022 Highland Schools Family Fun Night
Highland School Commons/Gymnasium, 1030 Cardinal Drive
5:00 p.m to 7:00 p.m.
Contact Highland School for more information at (608) 929-4525
April 2022 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
April 2022 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 28-29, 2022 Highland Community Schools Creativity Expo & K-12 Art Fair
Highland School District, 1030 Cardinal Dr
For more information contact Josh Tarrell or Mary Kay McCarthy or call (608) 929-4525
April 2022 Village Wide Garage Sales
Starting at 8 a.m. both days
MAY 2022
May 2022 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
May 2022 The Great Wine & Chocolate Trail - Spurgeon Vineyards & Winery
Pairing luscious chocolates with our Fine Wine
10:00 a.m. to 5:00 p.m. - Reservation required - $15 per person
16008 Pine Tree Rd, Highland WI 53543
Contact Spurgeon Vineyards & Winery for more information at (608) 929-7692
May 2022 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
2021 NOTICE OF BOARD OF REVIEW
May 2022 Highland Rodeo Club Fun Show
Highland Rodeo Grounds, 4907 Lagoon Rd
Show at 10:00 a.m.
Contact Sarah Winkler for more information (608) 341-7183 or
[email protected]
May 2022 St Philip Preservation Association
Mass In Honor of The Feast of St. Philip
St. Philip Church - 1011 Dodgeville St, Highland
Mass starts at 1:00 p.m. with a light luncheon after the Mass Snacks, beverages and desserts welcome to be brought in & shared in the lower level.
If you have any questions, you may call (608) 341-7665 or (608) 929-7490
or email [email protected]
May 2022 Highland Elementary Spring Concert
Highland Elementary School Gym
1030 Cardinal Drive, Highland
Contact the School Office for more info at (608) 929-4525
May 2022 Highland Fire Department Steak Feed
Highland Fire Station, 709 Dodgeville St, Highland WI
Serving from 5:00 p.m to 9:00 p.m. ~ $15 per meal
For local home delivery please call 929.4856 or 574.3030
Proceeds benefit the Fire Department Equipment & Training
For more information contact Bob Michek at (608) 574-3030
May 2022 4th Annual Public Square Rosary Rally
Ss. Anthony & Philip Church, 726 Main St, Highland WI
Starts at 12 Noon
Come join us to pray the rosary for our intentions and those of Our Blessed Mother!
We will be joining over 23,000 other sites who will be praying the rosary during that hour.
May 2022 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 21, 2022 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 24, 2024 8th Grade Graduation
Highland School Distrcit, 1030 Cardinal Drive
Contact Highland Schools for more information (608) 929-4525
June 2022
June 2022 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. - Reservation required - $15 per person
16008 Pine Tree Rd, Highland WI 53543
Contact Spurgeon Vineyards & Winery for more information at (608) 929-7692
June 2022 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 2022 3rd Annual Old School Block Party - Raising the Roof
Highland Area Historical Society, 526 Isabell St, Highland WI ~ FREE ADMISSION
All proceeds will benefit the Highland Area Historical Society
Contact Luke Drury at [email protected] with any questions etc...
July 2022
July 2022 American Legion Post 422 Picnic - held with VFW on June 13th
Highland Village Park, 755 Park St
Chix BBQ Dinner serving starts 11:00 a.m.
Contact Jim Esser for more information at (608) 929-4951
July 2022 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 2022 Our Town Celebration
Highland Lion's Club
Contact Mike Spink @ 608.574.4258 or Sheri Esser @ 608.553.1340 with questions or concerns.
July 2022 Way Cool Wine Days - Spurgeon Vineyards & Winery
Making mixers, Slushies and Wine-a-Ritas with our Fine Wine
10:00 a.m. to 5:00 p.m. - Reservation required - $15 per person
16008 Pine Tree Rd, Highland WI 53543
Contact Spurgeon Vineyards & Winery for more information at 608.929.7692
July 2022 Christ Lutheran Church
Annual Outdoor Christian Concert
Featuring music by...
Highland Village Park, 755 Park Street at 7:00 p.m.
In case of rain, the concert will be held at the Highland Historical Society Gym
Contact Julie Koss for more information at 608.623.2495