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 2019
August 30-September 1, 2019 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
September 19, 2019 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
September 20-21, 2019 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
September 28, 2019 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 2019
October 2019 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 12-13, 2019 29th Annual Harvest Festival
Spurgeon Vineyards & Winery
16008 Pine Tree Rd, Highland WI 53543
10:00 a.m. to 4:00 p.m.
Contact Spurgeon Vineyards & Winery for more information at (608) 929-7692
October 2019 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. ~ http://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
October 2019 3rd Annual Rosary Rally
Ss. Anthony & Philip Church grounds
Starts at Noon and lasts about 45 minutes
Bring your own chair, if you need one
This public rosary will be prayed for reparation to the Immaculate Heart of Mary, for our country and for would peace.
Please join us!
October 18, 19, 25 & 26, 2019 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 26, 2019 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 2019 Halloween Trick-or-Treating
Trick-or-Treating from
November 2019
November 2019 Veterans Breakfast
By the Veterans at the Red Zone
8:30 a.m. to 12:30 p.m.
Help us continue to serve our Community, Veterans, Military Families, Students and Others.
November 2019 Christ Lutheran Church Soup Supper
Serving 4:30 p.m. to 7:30 p.m.
303 Main Street, Highland WI
Chicken Noodle, Potato Ham and Chili
Cheese, bread, dessert & beverage
Adults - $9.00, Children - $4.00, Under 5 free
November 23-24, 2019 15th Annual Christmas Open House - Spurgeon Vineyards & Winery
16008 Pine Tree Rd, Highland WI 53543 ~ From 10:00 a.m. to 4:00 p.m.
Contact Spurgeon Vineyards & Winery for more information at (608) 929-7692
December 2019
December 6, 2019 Holidays in Highland Wagon Ride Caroling
Leaving from church parking lot (top of Main St) at 7:00 p.m.
Highland Girl Scouts will be serving hot cocoa and cookies
December 6, 2019 Holidays in Highland Home Outdoor Lighting & Decorating Contest
December 7, 2019 Holidays in Highland
Breakfast with Santa at Highland Fire Station - 8:00 a.m. to 11 a.m.
Craft & Vendor Fair at Highland School - 9:00 a.m. to 1:00 p.m.
Live Reindeer Exhibit - 430 p.m. to 7:30 p.m.
Spurgeon's Wine, Food & Music - 4:30 p.m. to 8:30 p.m.
Lighting of Luminaries - 6:00 p.m.
Tree Lighting Ceremony - 7:00 p.m.
Ugly Sweater Contest at The Bar Stool Sports Pub - 9:00 p.m.
December 17, 2019 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 19, 2019 Elementary 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 2020
January 2020 Highland Lion's Club Fisheree
Blackhawk Lake Recreation Area, 2025 County Road BH
Gates Open at 5:00 a.m. FREE PARK ADMISSION
Registration: 8:30 a.m.
Adult Fishing Contest: Register fish by 2:00 p.m.
Serving Breakfast: 8:00 a.m. to 10:00 a.m.
Kid's Learn to Fish: 9:00 a.m. to Noon
50/50 Drawing Hourly: 10:00 a.m. to 3:00 p.m.
Door Prize Drawing Starting 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)
Gun Raffle Drawing: 3:30 p.m.
GRAND PRIZE DRAWING: 4:00 p.m.
1st Prize: Wolf Pack Adventures Salmon Charter Fishing Expedition or $500
2nd Prize: Wolf Pack Adventures Walleye Charter Fishing Expedition or $300
3rd Prize: Vortex Ranger 1300 Laser Rangefinder
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
Tickets $1.00 each or 6 for $5.00
For more infomration please contact
Sheri Esser (608) 553-1340 or Mike Spink (608) 574-4258
February 2020
February 2020 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 2020 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 2020 Highland Ambulance Service Valentine's Breakfast
Highland School District Commons, 1030 Cardinal Drive
All you can eat...Serving at 8:00 a.m. til 12:30 p.m.
Adults $7.00 ~ K-8 $5.00 ~ Pre-School - Free
February 2020 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 senion earn a scholarship.
March 2020
March 2020 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 2020 Ss. Anthony & Philip's St. Pat's Dinner
Ss. Anthony & Philip Church, 726 Main St
Call (608) 929-7490 for more information
March 2020 Knights of Columbus Fish Fry
Ss. Anthony & Philip Church Basement, 726 Main St
Serving from 5:00 p.m to 8:00 p.m.
Carryout available until 7:00 p.m.
Contact Jim Esser for more information at (608) 929-4951
April 2020
April 7, 2020 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 2020 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 18, 2020 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 2020 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 2020 Highland Community Wide Garage Sales
Some sales are not held every day.
Thursday, April 25th - 8 a.m. to 5 p.m.
Friday, April 26th - 8 a.m. to 5 p.m.
Saturday, April 27th - 8 a.m. to 3 p.m.
April 2020 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]
Aug 30-May 1, 2020 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 2020
May 2020 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 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]
May 2020 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 2020 Highland Elementary Spring Concert
Highland Elementary School Gym
1030 Cardinal Drive, Highland
Contact the School Office for more info at (608) 929-4525
May 2020 Board of Review 6 p.m.
Highland Village Hall
530 Main St, Highland WI 53543
Contact the Village Office if you have any questions at (608) 929-7781
2019 NOTICE OF BOARD OF REVIEW
May 2020 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 2020 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 11, 2020 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 16, 2020 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 23-24, 2020 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 2020
June 2020 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 2020 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...
June 2020 The Cheesy Weekend Trail
Southwest Wisconsin - sampling wine and cheese 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
Contact Spurgeon Vineyards & Winery for more information at (608) 929-7692
June 2020 American Legion Post 422 Picnic
Highland Village Park, 755 Park St
Chix BBQ Dinner serving starts 11:00 a.m.
High School Softball Games 11:00 a.m. to 1:00 p.m.
Raffle Drawing at 2:00 p.m.
Contact Jim Esser for more information at (608) 929-4951
July 2020
July 2020 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 18-20, 2019 Our Town Celebration
Highland Lion's Club
Contact Mike Spink @ 608.574.4258 or Sheri Esser @ 608.553.1340 with questions or concerns.
July 2020 Village Wide Garage Sales
Starting at 8 a.m. both days
July 2020 The Wine Party Trail
Southwest Wisconsin - sampling wine mixers and party foods 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
Contact Spurgeon Vineyards & Winery for more information at 608.929.7692
July 2020 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
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 2020 The Wurst Wine Trail EVER
Southwest Wisconsin - Sampling wine & bratwurst 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 @ 608.929.7692
August 2020 8th Annual Highland Tractor & Truck Pull
Highland Rodeo Grounds, 4907 Lagoon Rd, Highland WI
Starts at 6:30 p.m.
Driver Meeting at 6:00 p.m.
Admission $10 - 6 and under FREE
For more information contact Dave Gates @ 608.732.6953