Roll out of the parking lot at 200 S Main Street on a Saturday morning and you're on the Glacial Drumlin State Trail within about thirty seconds. Olde Town Coffee House sits right at the edge of the lot, close enough that you can smell the coffee before you clip in. Head east and the pavement gives way to crushed limestone, the village falls behind, and you're riding through the low, cigar-shaped hills that give the trail its name. Frogs sing from the kettle ponds in late spring. Farmland opens up on both sides. It's a good ride, and most people who live here have already figured that out.
What almost nobody riding that trail on a Saturday realizes is that they're standing at the quiet end of a thirty-year-old promise the state hasn't kept yet, and that promise is finally getting a construction schedule.
The Trail Runs 52 Miles. Getting to It Doesn't.
The Glacial Drumlin State Trail, as the Wisconsin DNR describes it, runs 52 miles from Cottage Grove to Waukesha, threading through ten small towns and some of the oldest glacial topography in southeastern Wisconsin. If you're starting from the Cottage Grove end, that's 52 miles of continuous, mostly flat trail heading east, past Deerfield, past London, all the way to Lake Mills and beyond.
Head the other direction, toward Madison, and the trail simply stops existing. There's no path. There's no trail. There's a stretch of ordinary road.
Route guides that cover this gap are blunt about it. The suggested path from Madison's bike network to the Cottage Grove trailhead runs along Femrite Drive, Hope Road, Vilas Road, and Clark Street, a route one Wisconsin trail guide flags directly as "not an officially designated bike route or lane," warning riders they'll be "sharing the road with vehicles" for about 6.7 miles, with a shoulder that "can be narrow in places." Riders who've made that connection themselves describe it the same way. One review posted to a major trail directory called the roads between the Cottage Grove trailhead and Madison's Capital City Trail "the most difficult and dangerous part of the trip," citing fast traffic, no bike lane, and a detour around bridge construction on Femrite.
So the trail itself is 52 miles long. But if you live in Madison and want to reach it without a car, you're improvising on farm roads for the better part of seven miles first. Cottage Grove has been sitting at the genuine, functional edge of the regional trail network, not because the trail runs out here, but because the connection to the rest of the metro never got built.
The Gap Has a Paper Trail Going Back to 1996
Here's the part that changes the story. This gap isn't an oversight nobody's gotten around to. It's a known, named, decades-old commitment.
According to the City of Madison's own engineering project records, closing this exact gap has been the shared goal of a formal agreement between the City of Madison, the City of Fitchburg, Dane County, and the Wisconsin DNR since 1996. Thirty years. The project has a name now, the Capital City Path Extension, and it's described in city documents as covering the "remaining 6-mile 'missing link' between the Capital City Path and the Glacial Drumlin State Trail in the village of Cottage Grove."
The current segment under active engineering, Segment 4-6, runs from Vondron Road east to the interstate, with Dane County Parks and the DNR handling the portion east of I-39/90 that ties directly into the existing Cottage Grove trailhead. According to Madison's engineering department, bid letting for this segment is anticipated in January 2027, with construction running through 2027 and 2028.
When it's finished, the two trail systems stop being two trail systems. The document is explicit: completion turns this into part of a continuous 140-mile path across the state. Not a scenic loop. A through-route, with Cottage Grove's Main Street trailhead sitting at the hinge.
The Village Isn't Waiting Around Either
While the county and city work through a multi-year regional project, Cottage Grove has been quietly filling in its own local gaps.
Village budget records show construction already underway in 2026 on a new stretch of multi-use path along Buss Road and W. Cottage Grove Road, closing a missing link that connects to the Damascus Trail and, from there, to routes reaching Granite Ridge School and Glacial Drumlin Middle School. That last name isn't a coincidence. The middle school is named for the same trail that runs through the village's front door.
The village hired Wolf Paving, a Hartland-based contractor, in late March 2026 to handle both the new path segment and repaving on four residential streets, at a total cost of roughly $833,000, according to reporting on the project. It's a smaller scale than the county's 6-mile connector, but it's the same instinct: keep stitching the local path network together so it's ready to plug into whatever arrives from Madison.
A few concrete numbers, side by side:
- 52 miles of continuous Glacial Drumlin State Trail already exists, running east from Cottage Grove to Waukesha
- 6.7 miles of unmarked, shared-lane road riding currently separates that trailhead from Madison's own trail network
- 30 years have passed since Madison, Fitchburg, Dane County, and the Wisconsin DNR first agreed to close that gap
- January 2027 is the anticipated bid-letting date for the segment that finally closes it
What This Actually Changes for the Village
For anyone who already lives in Cottage Grove, the practical shift isn't cosmetic. Right now, if you want to ride from your driveway to downtown Madison entirely on trail, you can't. You either drive to a Madison trailhead first, or you spend close to seven miles on roads that trail guides themselves warn aren't built for cycling.
Once Segment 4-6 is built, that trip becomes continuous. A ride that starts at the coffee house on Main Street can end on the isthmus without the rider ever touching a shoulder built for cars. That's a different kind of commute option for anyone who bikes to work in Madison. It's a different kind of weekend for anyone who currently loads a bike rack just to reach a trail they already live minutes from. And it's a different kind of Saturday for kids at Glacial Drumlin Middle School, who'll eventually be able to reach a genuinely uninterrupted regional path system on the same bikes they ride to school.
None of this requires the village to change. Cottage Grove was incorporated in 1924, named, according to trail histories, for a grove of burr oak trees where an early settler named William Wells built a cottage. The trailhead has sat at Main Street since long before anyone in Dane County was thinking about a Capital City connector. What's changing isn't the place. It's the reach.
The frogs will still sing in the kettle ponds in May. Olde Town Coffee House will still be the first stop and the last one. The difference, by the time the 2027 construction schedule plays out, is what's on the other end of that ride.
If you're weighing what a village like this actually offers day to day, beyond a mailing address off I-94, this is the kind of thing worth knowing before you assume you've already seen the whole picture. I write about Cottage Grove and the rest of the Madison metro because the details that matter to daily life rarely show up in a listing description. If you want a longer conversation about what's changing in this corner of Dane County, or anywhere else in the metro, reach out to Josh Brost. Let's Connect.
