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 2020
August 2020 Highland Gridiron Club Fundraiser
Highland Fire Department, 709 Dodgeville St
The Highland Gridiron Club is holding a fundraiser event to raise
funds for continued support of our Highland football program.
For more information contact Greg Biba @ 608.574.1382
or Travis Halverson @ 608.341.6109
August 15 & 16, 2020 German Fest Days - Spurgeon Vineyards & Winery
Pairing Bratwurst and German Food with our Fine Wine
16008 Pine Tree Rd, Highland WI 53543
Contact Spurgeon Vineyards & Winery for more information @ 608.929.7692
August 29, 2020 7th Annual Highland Truck and Tractor Pull
Highland Rodeo Grounds, 4907 Lagoon Rd, Highland WI
Starts at 5:00 p.m.
For more information contact Dave Gates @ 608.732.6953
September 2020
September 5 & 6, 2020 The Great Wine & Chocolate Tasting - Spurgeon Vineyards & Winery
Pairing luscious chocolates with our Fine Wine
16008 Pine Tree Rd, Highland WI 53543
Contact Spurgeon Vineyards & Winery for more information @ 608.929.7692
Highland Firemen's Labor Day Picnic
Highland Village Park, 755 Park St
Chicken BBQ on Sunday serving starts at 11:00 a.m.
Contact Tom Michek for more information at (608) 929-4997
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
Highland High School Homecoming
Highland High School, 1030 Cardinal Dr
FRIDAY EVENING - Spirit Night 7:00 p.m. with Coronation, Skits & Yell
SATURDAY EVENTS
Parade at 11:00 a.m. on Main Street
Football Game at 2:00 p.m.
Dance 8:00 p.m. to 11:00 p.m. with Grand March at 8:30 p.m.
Contact Highland School for more info at (608) 929-4525
Ss Anthony & Philip Church Oktoberfest
Ss Anthony & Philip Church, 726 Main St 3:00 p.m. - 10:00 p.m.
Big Pumpkin Weigh-in at 3:00 p.m.
German Dinner at 5:00 p.m.
Pie Eating Contest at 6:30 p.m. (contestants will be auctioned off)
Live Auction at 7:00 p.m.
Call (608) 929-7490 for more information
October 2020
October 2020 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]
October 10 & 11, 2020 Harvest Festival - Spurgeon Vineyards & Winery
Live Music ~ Hot Food available ~ Free Winery Tours ~ Free Wine Tasting
16008 Pine Tree Rd, Highland WI 53543
Contact Spurgeon Vineyards & Winery for more information at (608) 929-7692
October 2020 Highland Community Haunted Hayride
5718 Hines Rd, Highland WI
Dusk to 10:00 p.m. weather permitting
Proceeds from Hayride go to Country Cardinals 4-H & Iowa County Suicide Prevention
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 2020 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
October 2020 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 2020 Halloween Trick-or-Treating
Girl Scouts Costume Party 1:00 p.m. to 3:00 p.m. at Highland School, costume judging at 2:00 p.m.
Trick-or-Treating from 3:00 p.m. to 6:00 p.m.
November 2020
November 2020 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 2020 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 2020 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 2020 Veterans Day Program
Highland Elementary Gym
Starts at 2:00 p.m.
November 21 & 22, 2020 Christmas Open House - Spurgeon Vineyards & Winery
Super Sale on Select Wines ~ Free Wine Tasting ~ Free Local Product Tasting
16008 Pine Tree Rd, Highland WI 53543
Contact Spurgeon Vineyards & Winery for more information at (608) 929-7692
December 2020
December 2020 Holidays in Highland Wagon Ride Caroling
Leaving from church parking lot (top of Main St)
December 2020 Holidays in Highland Home Outdoor Lighting & Decorating Contest
December 2020 Holidays in Highland - Tentative Events
Breakfast with Santa at Highland Fire Station
Chicken Poop Gamble
Holiday Craft & Vendor Fair at Highland School
Holiday Movies & Childcare at Highland School during the craft & vendor fair
Hot/Cold Luncheon at Highland School
Euchre Tournament at Bootleggers
Live Reindeer Exhibit, Santa & Mrs. Claus at Highland Park
Mulled Wine - Courtesy of Spurgeon's Vineyard at Highland Park
Luminary Ceremony at Highland Park
Tree Lighting Ceremony
Ugly Sweater Contest at The Bar Stool Sports Pub
December 2020 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 2020 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 2021
January 2021 Highland Lion's Club Fisheree
Blackhawk Lake Recreation Area, 2025 County Road BH
Gates Open at 5:00 a.m. FREE PARK ADMISSION
Adult Fishing Contest: Register fish by 2:00 p.m.
Kid's Learn to Ice Fish: 9:00 a.m. to Noon (kids up to age 15)
Pavilion Opening: 10:00 a.m.
Door Prizes Start at 11:00 a.m.
Meat Paddles: 12:00 p.m. to 3:00 p.m.
Euchre Tournament: 12:30 p.m. ($5.00 entry fee)
Live Auction: 3:30 p.m.
GRAND PRIZE DRAWING: 5:00 p.m.
Gun Raffle Drawing: Following Grand Prize
50/50 Drawings
Fisheree Raffle - Tickets: $1 each or 6/$5
1st Prize: Wolf Pack Adventures Salmon Charter Fishing Expedition or $500
2nd Prize: Pit Boss Memphis Ultimate 4-in-1 Gas & Charcoal Grill w/Smoker
3rd Prize: Wolf Pack Adventures Walleye Charter Fishing Expedition or $300
4th Prize: $100 Cash
Other Raffle Drawings Throughout the Day
Door Prizes donated by Local Businesses
Must be present to win door prizes
Unclaimed Prizes will be redrawn after Grand Prizes Drawing
For more infomration please contact
Sheri Esser (608) 553-1340 or Mike Spink (608) 574-4258
February 2021
February 2021 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 2021 Highland Ambulance Service Valentine's Breakfast
Highland School District Commons, 1030 Cardinal Drive
February 2021 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 2021 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 2021
March 2021 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 2021 Ss. Anthony & Philip's St. Pat's Dinner
Ss. Anthony & Philip Church, 726 Main St
Call (608) 929-7490 for more information
April 2021
April 6, 2021 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 2021 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 2021 Highland School Prom
Highland School, 1030 Cardinal Drive, Highland
Dance from 9:00 p.m. to Midnight
Grand March at 9:00 p.m.
Contact the School Office for more info at (608) 929-4525
April 2021 Driftless Wisconsin Wine & Cheese Trail
Southwest Wisconsin - Sampling Wine & Cheese at various wineries and creameries
from 10:00 a.m. to 5:00 p.m. ~ https://driftlesswinecheesetrail.com/
Local Winery on the Trail: Spurgeon Vineyards & Winery, 16008 Pine Tree Rd, Highland WI
Contact Spurgeon Vineyards & Winery for more information at (608) 929-7692
April 2021 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 2021 Highland Community Schools Creativity Expo & K-12 Art Fair
Highland School District, 1030 Cardinal Dr
Elementary School Gym
Come and help us celebrate all the hard work students have accomplished this past school year.
For more information contact Josh Tarrell or Mary Kay McCarthy or call (608) 929-4525
MAY 2021
May 2021 Open Book 3:30 p.m. to 5:30 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 2021 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 2021 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 2021 Highland Elementary Spring Concert
Highland Elementary School Gym
1030 Cardinal Drive, Highland
Contact the School Office for more info at (608) 929-4525
May 2021 Board of Review
Highland Village Hall
530 Main St, Highland WI 53543
Contact the Village Office if you have any questions at (608) 929-7781
May 2021 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 2021 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 2021 Middle School and High School Spring Concert
Highland Elementary Gym, 1030 Cardinal Dr
Concert at 7:00 p.m.
Contact Highland Schools for more information (608) 929-4525
May 2021 High School Graduation
Highland School Distrcit, 1030 Cardinal Dr
Commencement starts at 1:30p.m.
Contact Highland Schools for more information (608) 929-4525
May 2021 The Great Wine & Chocolate Trail
Southwest Wisconsin - Sampling wine & chocolate at various wineries
from 10:00 a.m. to 5:00 p.m. ~ www.southwestwisconsinwinetrail.com
Local Winery on the Trail: Spurgeon Vineyards & Winery, 16008 Pine Tree Rd, Highland WI
Contact Spurgeon Vineyards & Winery for more information at (608) 929-7692
June 2021
June 2021 Bring on the Bacon & Cheese Days - Spurgeon Vineyards & Winery
Pairing Prime bacon treats and Artisan Cheese with our Fine Wine
16008 Pine Tree Rd, Highland WI 53543
Contact Spurgeon Vineyards & Winery for more information at (608) 929-7692
June 2021 VFW Summerfest Picnic
Highland Village Park, 755 Park St
Serving Chicken BBQ Dinner starting at 5:00 p.m.
Refreshment Stand
Come out and support your local veterans!!!
June 2021 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 2021
Open Book 3:00 p.m. to 5:00 p.m.
Highland Village Hall
530 Main St, Highland WI 53543
Contact the Village Office if you have any questions at (608) 929-7781
July 2021 American Legion Post 422 Picnic
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 2021 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]
Board of Review starting 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
2020 NOTICE OF BOARD OF REVIEW
July 2021 Our Town Celebration
Highland Lion's Club
Contact Mike Spink @ 608.574.4258 or Sheri Esser @ 608.553.1340 with questions or concerns.
July 2021 Village Wide Garage Sales
Starting at 8 a.m. both days
July 2021 Way Cool Wine Days - Spurgeon Vineyards & Winery
Making mixers, Slushies and Wine-a-Ritas with our Fine Wine
16008 Pine Tree Rd, Highland WI 53543
Contact Spurgeon Vineyards & Winery for more information at 608.929.7692
July 2021 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