Southern Wisconsin Guided Trail Rides
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Nearby gyms & sports facilities
53562
Elmwood Avenue
W Washington Street, Milwaukee
Parmenter Street
Aurora Street
53562
53562
53562
Terrace Avenue
7734 Terrace Ave
Nearby health & beauty businesses
Terrace Avenue
Elmwood Avenue
Parmenter Street
Elmwood Avenue
-
Nearby beauty salons
Junction Road, Madison
N High Point Road
Madison
Terrace Avenue
Parmenter Street
Elmwood Avenue
Nearby hair salons
N High Point Road, Madison
Terrace Avenue
Parmenter Street
Elmwood Avenue
Elmwood Avenue
53562
Nearby nail salons
53562
Elmwood Avenue
N Butler, Madison
Deming Way
Deming Way
Deming Way
"Non Competitive and Fun Riding"
Open to ATV, UTV (Max. Width 65") and Dirt Bikes
Kid Friendly The trail consists of a 15-25 mile loop on private property.
Have 2 locations at which I host events 3 or 4 times a year so that you can get out and ride your ATV, UTV, or Dirt Bike. The Hill Point location is 50 miles N-W of Madison and Middleton location is 10 miles West of Madison. These rides consist of guided groups broken down by skill level, so everyone can ride at their own ability. The Hill Point event normally happens in Spring/Summer (mid May to mid June) because it being hunted during fall and Middleton events happen in Fall (October) after crops are harvested. Hill Point location is totally different than Middleton location. Hill Point with lots of elevation changes and being roughly 75% in the woods is more technical riding and slower course. Versus Middleton 75% field riding on relatively flat terrain compared to Hill Point is a little less technical riding and faster course. Both rides have there points and people like both locations.
- Both location have single track sections for two wheel machines for people that want more technical dirt bike riding.
- At an additional cost, lunch is often offered by local group in Middleton.
- Events are limited to 100 machines. Call Dan for more information at (608) 445-8228 7am to 10pm. Sister event link that uses the same course after being conditioned by guided trail riders in Middleton is:
*** Southern Wisconsin Off Road Bicycles Rides ***
https://www.facebook.com/SWORBR/about/?ref=page_internal
2 of 2 “Video Of The Day” is a tie from final trail ride of the year on Sunday, October 18, 2026.
“Follow” the page if interested in staying in the loop for future events. 
 Sorry about the wind noise as it was last minute decision to videotape!
1 of 2 “Video Of The Day” is a tie from final trail ride of the year on Sunday, October 18, 2026.
“Follow” the page if interested in staying in the loop for future events. 
100% a go for Sunday, October 18 trail ride!
NEW SINGLE TRACK 100% READY TO RIDE TOO!
Friday, October 16 Video 2 of 2
Saturday’s ride rescheduled
to Sunday, October 18th, 2026.
Still have room for a few more machines details to pre-register are in October 5 post full details are in “Event” post.
Have a few hours and want to help cut new single track on Saturday, October 17 for Sunday, October 18?
(2 hour minimum starting at top of the hour)
Working from 9:00 to 4:00? Call Dan at (608) 445-8228 (anytime)
Friday, October 16 Video 1 of 2
Saturday’s ride rescheduled
to Sunday, October 18th, 2026.
Still have room for a few more machines details to pre-register are in October 5 post full details are in “Event” post.
Ride rescheduled to Sunday, October 18!
Only contact me if pre-registered and you can’t make it Sunday!
2026 Last Call: For Saturday, October 17 with “Southern Wisconsin Guided Trail Rides”.
1) Still have room for more machines!
2) Weather forecast is perfect for Saturday for riding off-road.
3) Don’t wake up Sunday morning wishing you would’ve did the ride on Saturday!
4) Pre-registered now! So we can plan accordingly for day of ride.
Pre-registration details were posted on October 5. Complete event details are in “Event Posting”.
Forecast for this Saturday final event
for 2026 is looking perfect for riding!
SUNNY AND 57 DEGREES
Pre-register now so Lori can plan for food amount needed!
(Look at October 5 post for details to preregister.)
Like to add new smaller wood section before Saturday!
Anybody got some free time to volunteer to help make it happen?
Call me at:
(608) 445-8228 7am to 10pm.
10/11/2026
Sorry about wind noise in video!
Six-year-old Vince says "Thank You" for the opportunity to play with his dad and grandpa for second year in a row! Three generations how cool is that?
Last opportunity to make memories in 2026 with “Southern Wisconsin Guided Trail Rides” is Saturday, October 17 weather permitting.
People that participated in past events, including, October 10 please leave a comment and photo (if possible)
to challenge people to sign up for final ride on Saturday, October 17, 2026.
Side note:
Like to thank people that signed the card for for Lori as her husband Art passed away unexpectedly in January. She was very grateful and appreciative to receive it!
10/10/2026
Confirmation ride is 100% a go for Saturday, October 10, 2026.
Weather is going to be excellent.
Still have room for more machines!
Ride starts at 10 am can sign up until noon.
If coming after official start time text me at 608-445-8228 so we are aware you’re coming later. Name and number of people and machines needed in text.
Other details:
1) Please sign the card by sign up for Lori. Lori’s husband Art passed away unexpectedly in January 2026. Please make a note and include miles traveled to ride location, roughly.
Art and Lori have supported the ride from day one which is been 18 years and Lori has been coordinating the lunch on site for many years. Both very much appreciated.
2) Participating landowner is looking for some used riding boots and possibly chest protectors as their kids have recently started dirt biking ladies boots size 8 1/2 or men’s 7 1/2 and kids size 6.
3) Participating land owners have a few ATVs for sale.
2020 Yamaha grizzly 700
(details in photo)
2017 Polaris 110
(price 3000 roughly)
Both machines are in very nice condition if interested reach out to me at 608-445-8228.
Click here to claim your Sponsored Listing.
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Middleton, WI
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