The newest trailhead in Oconomowoc is a parking lot on West 2nd Street, just south of 1101 W. Second St. On Thursday, September 3, about 50 people gathered there to watch Mayor Matt Rosek cut the ribbon that joined the Watertown-Oconomowoc Interurban Trail to Waukesha County's Lake Country Trail. After the speeches, the first people onto the finished path were a group of local kids on bikes, racing up and down it.
For years the Lake Country Trail ended at Roosevelt Park. Riders heading west from Oconomowoc either turned around there or rode county roads. Now Oconomowoc sits in the middle of a continuous route. Delafield and Pewaukee lie to the east on the existing trail, and Watertown lies to the west on the new one. The Jefferson County announcement counted nearly 12.5 miles of new trail connecting the two counties.
To ride that middle stretch, you need to know the part of the route the announcements don't stress. A few blocks of it are city streets.
The link to Roosevelt Park runs on W. 2nd and S. Franklin
The new off-road pavement ends at the W. 2nd Street lot. According to Waukesha County's project description, cyclists continue on the road from there, following bike route signs on W. 2nd Street and S. Franklin Street until they rejoin the existing Lake Country Trail at Roosevelt Park. Walkers get a separate path. A sidewalk runs from the trail near W. 2nd Street, parallel to the street, and meets the existing sidewalk at S. Elm Street.
So the trip from downtown to the new trail has a short on-street section. The bike route is signed and only a few blocks long, but it is shared with traffic. That matters if you're riding with young kids or pushing a trailer. It also explains the new parking lot. If you want to start right on the off-road pavement and skip the street section, W. 2nd Street is where you park.
Heading east toward Delafield works the same way in reverse. You follow the signs back through town to Roosevelt Park, and the existing 14.5-mile Lake Country Trail picks up from there.
Why Oconomowoc's end was the last piece
The counties finished the trail from the Watertown end toward Oconomowoc. Jefferson County Parks Director Kevin Wiesmann told the Watertown Daily Times that county UW-Extension agents first pointed to the corridor as an opportunity in the early 1970s. In his words, the trail is "literally 50 years in the making." Over nine years, the Interurban cost $5.67 million. Wiesmann called it the largest single capital project the Jefferson County Parks Department has ever done.
The first section in Watertown came about through the work of the late Richard "Augie" Tietz, a former Jefferson County Board supervisor. A bench on that early stretch honors him. His children came to the September ribbon cutting. "The Lake Country/Interurban connection is the culmination of efforts throughout the years by Waukesha and Jefferson counties," Mayor Rosek said. "We are pleased that the City of Oconomowoc was able to help with the last section."
The project supporters include several names from close to home: Oconomowoc Rotary, the Earl and Eugenia Quirk Foundation, and the Greater Watertown Community Health Foundation. We Energies, WisDOT, and the DNR are also on the list.
The route west, in order
Here is the trip from the W. 2nd Street lot to Watertown, with the Jefferson County phases listed in the order you'll ride them:
- Lake Country Trail Phase 5, about 1.2 miles. This section is 10-foot-wide asphalt laid inside an existing We Energies utility corridor. It runs from W. 2nd Street to the Jefferson County line.
- County Hwy F to 2nd Street, about 4 miles. This is the final Interurban phase, the one that ties Watertown, Ixonia, and Oconomowoc together.
- River Road to County Hwy F, about 4.8 miles. Jefferson County's pocket map labels Pipersville and Ixonia along the corridor.
- Humboldt Street to River Road, about 2.25 miles. This oldest section brings you into Watertown.
- The Watertown trailhead at Clark and Humboldt streets. Watertown Daily Times reports have given it two different Humboldt Street numbers, so the cross streets are the more reliable way to find it.
The whole Jefferson County section is paved, about 11 miles of it, so no crushed stone is reported anywhere on the new connection. It runs through what Wiesmann calls "some of our most beautiful landscapes" in rural Jefferson County.
The two Rock River bridges
The route crosses the Rock River twice, on bridges built just for the trail. The three-span bridge sits just outside Watertown, and the two-span bridge sits just outside Oconomowoc.
"They're on old train trestle foundations, and you get a really cool sweeping panoramic view that's relatively unobstructed…I think those are two really cool destinations to reach when you're biking either from Watertown or Oconomowoc." — Kevin Wiesmann, Jefferson County Parks Director
The two-span bridge is the closer of the two, which makes it a natural turnaround for a shorter out-and-back from the W. 2nd Street lot. Riding the full route gets you both crossings, with Watertown at the far end.
Places to stop at each end
The Clark Street trailhead in Watertown has parking, a restroom, a water-bottle filler, bike racks, wayfinding signs, and a repair station. Watertown's tourism office listed those amenities before the final segment opened, so check current conditions when you go. Nearby, Bentzin Family Town Square offers riverside kayak access downtown. Riverside Park sits along the Rock River with barbecue grills, benches, and tables.
Downtown Watertown spots worth planning around:
- Literatus & Co., 401 E. Main St. A bookstore-café serving coffee, pastries, breakfast, and lunch. Its website lists 7 a.m. to 8 p.m. Monday through Saturday and 8 a.m. to 5 p.m. Sunday.
- Latte Donatte, 501 E. Main St. A café and bakery with a patio. Posted hours are 6 a.m. to 6 p.m. weekdays and 7 a.m. to 5 p.m. weekends.
- The Goose & Gander Pub and Grill, 200 N. 2nd St. A German-style pub with food and craft beer. It opened in early February 2026, and a May review listed it as open Wednesday through Saturday.
- Silver Moon, 1601 East Gate Dr. A riverfront restaurant a bit farther from the downtown cluster. Visit Watertown's September 2026 review describes its patio and cocktails.
On the Oconomowoc end, the on-street link leads back toward downtown. Roots Coffeebar & Cafe, at 124 E. Wisconsin Ave., serves coffee, bakery items, sandwiches, soups, and salads. It's open 6:30 a.m. to 5 p.m. on weekdays and 7 a.m. to 3 p.m. on weekends. For dinner after a late ride, Lago Su Bella at 126 W. Wisconsin Ave. serves Italian Tuesday through Sunday and is closed Mondays. Hours change, so check before you set out.
Fall and winter rules on the new path
Each county runs its own section, so the rules depend on which side of the county line you're on:
- Passes. Waukesha County lists the Lake Country Trail among its trails that need no annual membership or daily permit. Jefferson County's Interurban page lists no trail-use fee.
- Hours. By ordinance, Jefferson County closes its park trails and bike paths from 10 p.m. to 5 a.m. With October evenings getting dark earlier, that matters more for anyone riding back late from dinner in Watertown.
- Winter biking. Waukesha County lists the Lake Country Trail as open to fat-tire biking in winter. Its winter materials don't promise snow clearing on the new connection.
- Skiing and snowmobiles. Neither county lists this corridor as a cross-country ski trail. Jefferson County asks snowmobilers to stay on marked snowmobile routes, and the paved Interurban isn't designated as one.
The trail was already drawing distance riders before the ribbon cutting. One had ridden the finished sections for two years; at the ceremony, the rider described the trail as beautiful and said it was possible to ride from home to Watertown.
If you or someone close to you is weighing a move around Oconomowoc and trail access is on the list, Jenna Johanning is glad to walk through how close different streets sit to the W. 2nd Street lot and Roosevelt Park. Schedule a consultation.
This article is general information, not legal, tax or financial advice. Consult a qualified professional about your situation.
