Looking for local route recommendations? We got you. This is a curated collection of the very best road, mountain, and family rides in the area, complete with digital route maps!
Distance: 14.2 mi
Difficulty: Easy
Elevation: +/– 796 FT
Start at Hometown Junction Park in Verona, then cruise through farmland and the artist’s enclave of Paoli. Stop there for coffee and a snack, and hit up the eclectic cafes, galleries, and shops before heading back to Verona. This is a fun option for younger riders familiar with hand signals and riding with traffic, or for anyone looking for a short, casual loop.
Distance: 15.7 mi
Difficulty: Easy
Elevation: +/– 789 FT
If you need a reason beyond beer to stop in at the Capital Brewery, this quick-and-easy route is a great one—and will make that beer taste all the better. You’ll start and finish at the Middleton brewery and travel through town before hitting quiet country roads along some of Dane County’s lushest farmland. Say hi to the cows.
Distance: 19.9 mi
Difficulty: Easy
Elevation: +/– 656 FT
From the Henry Vilas Zoo, cruise along this flat route made up of bike paths and local roads through the restored prairies, savannas, and woodlands of the University of Wisconsin Arboretum. Midway through the ride you’ll come to the city of Fitchburg, named a 2012 Bicycle Friendly Community by the League of American Bicyclists. After your ride, watch the polar bears paddle underwater while you grab a snack at the zoo café.
Distance: 19.8 mi
Difficulty: Easy
Elevation: +/– 920 FT
Staff at our Madison West store recommend this route to customers after they buy their first road bike. At just under 20 miles and relatively flat with minimal turns, it showcases the area’s rolling farmland and suburban neighborhoods—and is an excellent option for breaking in new gear. Start at Point Burger Bar in Middleton and loop out to Cross Plains before heading back.
Distance: 24.6 mi
Difficulty: Easy
Elevation: +/– 833 FT
This loop is mostly flat and almost all picturesque, the perfect route for a casual ramble or a recovery day. You’ll ride south along the shores of Lake Monona, through the Capital Springs State Recreation area, across the Boardwalk Bridge over Lake Waubesa, and along country roads surrounded on either side by cornfields and cow pastures. Start and finish at Olbrich Botanical Gardens.
Distance: 24.8 mi
Difficulty: Easy
Elevation: +/– 675 FT
This flat, lightly trafficked route from Olin Park on Lake Monona follows the Capital City Trail* out of Madison and onto the Lower Yahara River Trail through the Capital Springs State Recreation Area and into the town of McFarland. From there, you’ll head south through some of Dane County’s prettiest farmland, then swing wide through the Waubesa Wetlands State Natural Area as you loop back up to Madison. It’s a great route for new riders or anyone looking for a stress-free outing.
*State trail pass required: $25 annual, $5 daily
Distance: 29.9 mi
Difficulty: Easy
Elevation: +/– 1,024 FT
This straightforward and relatively flat route from the east Madison Trek store takes you onto quiet roads through the verdant farmland east of Madison. Expect cows, cornfields, and very few cars. It’s a great weekday loop when you’re pressed for time.
Distance: 33.1 mi
Difficulty: Moderate
Elevation: +/– 1,529 FT
Follow the well-traveled roads of Madison’s west side through West Middleton, south to Riley, and into Verona. The highlight of this route is the Wisconsin Brewing Company, a state-of-the-art facility in the Verona Technology Park where you can observe the kegs and fermentation tanks while you kick back with a cold one in the 12-tap tasting room. Start and finish at the west Madison Trek store.
Distance: 34.3 mi
Difficulty: Easy to Moderate
Elevation: +/– 1,140 FT
Head east then south on this flat-to-rolling route through the dairy farms and croplands of Dane County. The roads will be quiet, the cars will be few, the cows will be many. At mile 19, hang a right toward Cottage Grove, where you’ll find several options to refuel before looping back northeast. Several times along the route you’ll cross the Glacial Drumlin Trail, a 52-mile repurposed railbed worth exploring if you have time and a trail pass*.
*State trail pass required: $25 annual, $5 daily
Distance: 37.8 mi
Difficulty: Moderate
Elevation: +/– 1,096 FT
From Panera Bread in Fitchburg you’ll follow bike paths and quiet rural roads through the Brooklyn Wildlife Area and the village of Belleville—and consider a detour into town to ride along the 3,130-foot berm that separates Lake Belle View and the Sugar River. Continue through the community of Paoli with its quirky collection of art galleries, brew pubs, and shops, before heading back to Fitchburg where you can close out the ride with a craft beer at the Great Dane Pub and Brewing Company.
Distance: 47 mi
Difficulty: Moderate
Elevation: +/– 1,860 FT
This gently rolling route makes a great weekend outing into the pastoral farmland east of downtown. Start at the eastside outpost of the Great Dane Pub and Brewing Company. You’ll cruise along quiet roads flanked by cornfields and pastureland before heading south on Ridge Road toward Cottage Grove, then back to the Great Dane. Grab a donut at Schuster’s Farm, but save room to refuel from the brewery’s extensive food menu.
Distance: 49.5 mi
Difficulty: Moderate
Elevation: +/– 1,533 FT
Roll through picturesque farmland and sleepy small towns—and visit one uniquely Wisconsin attraction along the way. Start at Henry Vilas Zoo and head west past Lake Wingra and the University of Wisconsin Arboretum. Pass through the town of Verona, and at about mile 27, hang a left toward Mount Horeb and its famous Trollway: a collection of more than 20 larger-than-life carved wooden trolls that line the main street. Grab lunch or a snack at one of Mount Horeb’s bustling cafes, pick up a troll souvenir at Open House Imports, then follow the Military Ridge State Trail* back to the zoo.
*State trail pass required: $25 annual, $5 daily
Distance: 52.8 mi
Difficulty: Moderate
Elevation: +/– 2,181 FT
This is a great weekend outing that hits local favorites including the artist’s enclave of Paoli (check out the galleries and the eclectic 1 OAK Bicycles), the tiny town of Riley, and the hills around Mount Vernon and West Middleton. Start at the Henry Vilas Zoo and hop on the Southwest Commuter Path for a few miles before hitting the Capital City Trail*. Then follow quiet country roads through the hills of Dane County and finally back to Madison.
*State trail pass required: $25 annual, $5 daily
Distance: 55.6 mi
Difficulty: Moderate to Hard
Elevation: +/– 2,330 FT
Ride the same course as the competitors in the Madison Half Ironman, whose participants rank Madison as a Top Ten Host City. Head south on the Capital City Trail* and follow scenic country roads through the village of Oregon. Then head west over Observatory Hill, a climb just under a mile. You’ll come back through Paoli and past the Alliant Energy Center, then finish on the bike trail under John Nolen Drive to Olin Park.
*State trail pass required: $25 annual, $5 daily
Distance: 56.5 mi
Difficulty: Moderate
Elevation: +/– 2,610 FT
Take out-of-town guests on this half-day outing that’s punctuated midway with a quick out-and-back Wisconsin River crossing on the free Merrimac Ferry. (Because, why not?) Grab snacks from the ice cream/concession shops on either side of river, then follow the route south to the Wollersheim Winery and Distillery for a tour and tasting. Start and finish at the Pheasant Branch Conservancy.
Distance: 58 mi
Difficulty: Moderate to Hard
Elevation: +/– 1,772 FT
Park at the Henry Vilas Zoo and cruise through the University of Wisconsin Arboretum south through the town of Oregon, past the Badfish Creek State Wildlife Area, to the historic village of Stoughton on the Yahara River. Stoughton is known for its Norwegian heritage and calls itself “the birthplace of the coffee break.” An espresso stop in town is pretty much mandatory—and an ideal opportunity to suss out the story behind this bold coffee claim.
Distance: 61.7 mi
Difficulty: Hard
Elevation: +/– 3,771 FT
Head out from the west Madison Trek store on the bucolic, winding roads of Dane County. The route is rolling until mile 30, when you get to Blue Mound State Park*. Enter the park and prepare to climb one of the highest peaks in southern Wisconsin: Mounds Park Road is a little over three miles with a 5.5% average grade and tops out at about 1,700 feet. At the summit you’ll be rewarded with panoramic views of the Wisconsin River valley, the Baraboo Range, and the city of Madison to the east.
*Vehicle admission sticker required: $28 annual, $8 daily
Distance: 69 mi
Difficulty: Moderate to Hard
Elevation: +/– 2,446 FT
This is a great half-day jaunt into Dane and Jefferson counties. From Olbrich Botanical Gardens on Lake Monona, you’ll head northeast on mostly country roads bordered by farmland toward Waterloo, home of Trek Bicycle. Stop at Waterloo Firemen’s Park about a mile past Trek HQ, where you can refill your water bottles and use the restrooms. Then head due south to Lake Ripley and the quaint village of Cambridge before looping back to Madison.
Distance: 72.7 mi
Difficulty: Hard
Elevation: +/– 4,574 FT
This route is a local favorite. The highlight is the picturesque town of New Glarus, also known as Little Switzerland for its Alpine chalet-style architecture. Start at Blackhawk Park west of Madison and wind your way on rolling terrain (read: almost no flat sections) down to New Glarus. A stop at New Glarus Brewing Company is a must, but be warned: You still have lots of climbing to do before the ride is over. Start and finish at the west Madison Trek store.
Distance: 103 mi
Difficulty: Hard
Elevation: +/– 6,011 FT
Start at Lakeview Park in Middleton and follow this epic rolling route north through some of the area’s most beautiful farmland and legendary climbs. At mile 26 and again at mile 71, take the free, seven-minute ride on the Merrimac Ferry across Lake Wisconsin. Miles 31 to 41 take you along the shaded roads of Devil’s Lake State Park* (look for the iconic pink-tinted quartzite bluffs) where you’ll find concessions at the north and south ends of the lake, as well as restrooms and shelters. Bust out your bike-packing gear and make this a weekend adventure: The park boasts three public campgrounds ($20; reserve at devilslakewisconsin.com).
*Vehicle admission sticker required: $28 annual, $13 daily, $5 hourly
Distance: 106.9 mi
Difficulty: Hard
Elevation: +/– 4,414 FT
Bring your climbing legs—the lollipop-shaped Ironman Wisconsin course is the hilliest in North America. Start at the Alliant Energy Center and ride south through Fitchburg, then west through Verona. At about mile 12, you’ll begin a roughly 45-mile loop that will take you up some of rural Dane County’s most notorious climbs including Barlow Hill and Garfoot Hill. Tackle the loop twice like the Ironman competitors, or head back on the lollipop stick for a 62-mile day.
Distance: 111 mi
Difficulty: Hard
Elevation: +/– 4,550 FT
Breathtaking views (lots of climbing) and quiet country roads make this 111-miler a local favorite. Start at Maple Bluff on Lake Mendota and head southwest through the town of Mazomanie (plenty of convenience store options for restrooms and snacks) and on to Spring Green, home of the Frank Lloyd Wright estate, Taliesin. From there, head northeast through Sauk City (more refueling options) on your way back to Madison.
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