What does Madison, Wisconsin, have in common with Amsterdam, Copenhagen, and Montreal? They are amongst the “Best Places on Earth to Bike,” according to Yahoo Travel. With temperate summer weather, over 200 miles of bike paths, five lakes, and the most parks per capita in the US, it’s easy to see why Madison received a Platinum designation by the League of American Bicyclists and ranks as one of the five best US cities for biking.

We worked with local officials and bike activists to build our guide to biking in Madison, Wisconsin, and have personally ridden the majority of the paths and routes highlighted in this article. Whether you’re a local looking to find new places to ride or a vacation cyclist looking for a destination with world-class food and exceptional experiences, this guide is for you!

Madison Bike Map

This interactive Madison Bike Map includes all the bike routes, trails, and points of interest called out in this guide. It’s built using native Google pins, so click to take a virtual Madison bike tour, including crowd-sourced photos and reviews. The Select Bike Benefits and BCycle Station layers are defaulted off, but feel free to click on and off different layers and zoom in and out to make this map work for you.

Google technology allows you to click in and load this map on your cell phone with live GPS position updates, but use your best judgment between what you see with your eyes and a map from the internet. If the map doesn’t load, refresh the page. We think it’s worth it

Featured Madison Bike Paths

With so many Madison bike paths, knowing where to start riding can be difficult. The City of Madison’s Bike Madison page has a lot of information, perhaps too much. We will break it down for you. Here’s the skinny.

The greater Madison region has nine premier bike paths:

• Glacial Drumlin State Trail (52.8 miles, crushed stone)
• Military Ridge State Trail (42.1 miles, 3.6 miles paved)
• Badger State Trail (40 miles, 6 miles paved)
• Sugar River State Trail (22 miles, crushed stone)
• Capital City Trail (17 miles, paved)
• Southwest Commuter Path (5.75 miles, paved)
• Lower Yahara River Trail (5.5 miles, paved)
• Cannonball Path (3.5 miles, paved)
• Howard Temin Lakeshore Path (2 miles, mostly paved)

This section covers the bike trails in Madison longer than 10 miles. The rest are discussed in the Madison by Bike Routes and Madison Loop Ride sections. Please note – A State Trail Pass is required for all people age 16 or older biking on certain trails, including all state trails listed here.

Glacial Drumlin State Trail (52.8 miles, unpaved)

The Glacial Drumlin State Trail runs between Wisconsin’s two largest urban areas, Madison and Milwaukee. It follows an abandoned rail corridor for 52 miles through farmlands and glacial topography and connects ten small towns from Cottage Grove to Waukesha. It has a crushed stone surface suitable for 32mm tires or wider, except for a short, 1.5-mile, on-road section northeast of Jefferson.

There is a direct connection on the east end of the trail into the Milwaukee bike system, but there’s a gap between Cottage Grove and the Madison bike system at the Cottage Grove terminus. A popular Madison bike ride is to start at Cottage Grove and bike 16 miles to Sandy Beach and back (32-mile round trip).

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Military Ridge State Trail (42.1 miles, 3.6 miles paved)

Military Ridge State Trail travels from Madison to Dodgeville via an 1855 military route, including stops at Governor Dodge and Blue Mound state parks. The trail is paved for the first 3.6 miles until the Badger Prairie Community Garden in Verona. From there, it’s a crushed stone trail suitable for 32mm tires that passes through agricultural lands, woods, wetlands, and prairies, as well as the trail towns of Verona and Mt Horeb.

A classic ride is a lunch run to Riley Tavern, which is a 21-mile out-and-back from The Velo UnderRound. Ardent riders might want to challenge the climb in Blue Mound State Park on the largest hill in the southern half of the state. The segment from the guardhouse to the top has an average grade of 10% with a maximum of over 20% (yikes!).

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Badger State Trail (40 miles, 6 miles paved)

The Badger State Trail stretches 40 miles from Madison and the Wisconsin-Illinois border, where it turns into the 17-mile Jane Addams Trail. That’s 57 miles, possibly more if you venture onto the Sugar River State Trail. The trail is paved for the first 6 miles until you reach Purcell Rd. From there, it’s a crushed gravel path. Also, as of 2023, the trail is closed at the Steward Tunnel, with a state-provided Tunnel Road detour shown.

A fabulous Badger State Trail ride is an out-and-back to New Glarus Brewing Company. Be sure to stop in for a tour and perhaps a pint of their only-sold-in-Wisconsin Spotted Cow Ale. That’s a 43-mile out-and-back from the Velo UnderRound.

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Sugar River State Trail (22 miles, crushed stone)

The Sugar River State Trail is a 24-mile crushed gravel path following an abandoned railroad line from New Glarus to Brodhead. The trail has 14 trestle bridges as it crosses the Sugar River and its tributaries.

The Sugar River Trail is approximately 20 miles south of Madison on the Badger Trail, so that’s a beefy ride for casual cyclists. Many people shuttle their bikes down for an out-and-back on the Sugar River Trail or utilize the Badger Trail to form an 11-mile loop from New Glarus.

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Capital City Trail (17 miles, paved)

The Capital City Trail is the last, but certainly not least, of the featured Madison bike paths. It’s the only 100% paved feature path and connects the Military Ridge State Trail, Badger State Trail, and, eventually, the Glacial Drumlin State Trail.

There are too many features and rides along the Capital City Trail to mention here, but you’ll find more details in these sections:

• Madison By Bike → Capital City Trail
• Loop Rides in Madison → Lake Monona Bike Loop
• Loop Rides in Madison → Capital City Loop
• Loop Rides in Madison → Monona Bay Loop

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Madison By Bike

Madison By Bike is a Destination Madison initiative to get people out riding and exploring the city. They’ve created four feature rides (with four unique vibes) that showcase the best of Madison. An app-like page lets you collect exclusive discounts and earn prizes as you travel their curated routes.

We made a point to ride every route and make all the check-ins, and it was loads of fun. The discounts at the participating restaurants were legit, and we saw things we never would have noticed without the check-in game (you can even use your accumulated points to donate to Free Bikes 4 Kidz Madison or enter to win an e-bike for yourself!). If you’re new to town, you have to check it out, and we wager even a veteran rider may learn a thing or two from Madison By Bike.

Capital City Trail (4.8 miles One-Way)

The Capital City Trail is basically the Cap City Trail from Turville Bay to Starkweather Brewing Company – aka Lakeshore Views to Brews. Consider parking at Olin Park and staying on the Cap City Trail to Olbrich Botanical Gardens.

Route Highlights include:

• Monona Terrace – The last significant Frank Lloyd Wright building, designed in 1938 but not completed until 1997.
• Monroe Street Neighborhood – A vibrant and iconic community along ten blocks of Williamson Street (aka Willy Street) that’s been called Bohemian, Hippie, Green, Hipster, and even sometimes the Marquette Neighborhood. Check-in and discounts: Alimentari, Working Draft Beer Company, Weary Traveler Freehouse, and Greenlife Trading Company.
• Atwood Neighborhood – A funky and diverse near-eastside neighborhood with check-in and discounts at Monty’s Blue Plate Diner, Fortune Favors, and Starkweather Brewing Company.
• Olbrich Botanical Gardens – a free 16-acre urban garden. (note – check Bicycle Benefits for free entrance to the Bolz Conservatory)

Southwest Commuter Path (3 miles One-Way)

The Southwest Commuter Path follows a trail by the same name. The physical trail is on an old railbed designed to be isolated from the neighborhood with a series of underpasses.

The Madison By Bike route encourages you to get out and explore by adding check-ins along the way:

• Monroe Street Neighborhood – Madison’s “first suburb” with a quaint and distinct feel from its proximity to the university. Be sure to check out the MBB discounts at Wingra Boats, cute and quirky Zip-Dang, and the award-winning Orange Tree Imports.
• Camp Randall Stadium – The oldest stadium in the Big Ten
• Madison Train Depot – Home to Bandit Tacos and Coffee
• Brittingham Beach – Be sure to check in at Brittingham Boats

Lakeshore Path (2 miles One-Way)

The Lakeshore Path route follows the Howard Temin Lakeshore Path from the Memorial Union Terrace to Picnic Point through the University of Wisconsin campus. This route is only partially paved with a hard-pack surface suitable for most bikes, but it could get muddy in inclement weather. You can’t bike to Picnic Point, but there’s a bike rack and BCycle station right out front. Also, you might consider riding an interior route back on bike lanes of Observatory Drive to form a loop and check in at Allen Centennial Garden and the effigy mounds.

Check-ins include:

• Memorial Union Terrace – Elevated views of Lake Monona and home to the iconic sunburst chairs
• Lakeshore Nature Preserve – A great place to hike with lake views and fire pits along the way to Picnic Point
• Allen Centennial Garden – A small but vibrant garden
• Observatory Hill Effigy – If you look carefully, you’ll see the remnants of two effigy mounds

Fitchburg – Cannonball Loop (10.1 miles – Loop)

The Fitchburg-Cannonball Loop might be the most complete ride of the Madison By Bike portfolio. You access via Fitchburg, a near-city trail town on the Capital City Trail, and form a loop via the Cannonball Path Trail and McCaffy/Arboretum Drive. Loop rides have a certain je ne sais quoi compared to out-and-backs, especially when the neighborhood connecting roads are slow and mellow.

Check-ins include:

• Fitchburg Restaurants – Check-in for discounts at Thirsty Goat or Enrique’s Grill
• Wheel & Sprocket – Bike accessories and expert fitting… maybe even a test ride on your soon-to-be next e-bike
• Velo UnderRound – The junction of five of Madison’s favorite trails: Capital City State Trail, Southwest Commuter Path, Military Ridge State Trail, Badger State Trail, and Cannonball Path
• University of Wisconsin Madison Arboretum – More than 17 miles of trails through restored prairies, savannas, woodlands, and wetlands, but please note that bikes are only permitted on the park roads.

Loop Rides in Madison

Native Americans called Madison Teejop which is how the Hoocąk people refer to the land. Its translated meaning is, “land of the four lakes” (Mendota, Monona, Waubesa, and Kegonsa). Madison’s city center is built on an isthmus between Lake Mendota and Lake Monona. All this water provides beautiful views and motivates city planners to reduce car traffic and parking pressure. It also allows bike paths to naturally form bike loops instead of the hub and spoke design that develops in most river-based cities.

Chris Quinn of Machinery Row Bicycles told us – “Dane County is very alert, awake, and aware of bicycles.” He attributes part of the friendly bike culture to local industries like Trek (Waterloo, Wi), Planet Bike, and Saris. He also pointed out that Machinery Row rents hybrid bikes suitable for longer rides. His pro-tip:

with some planning, you could get an evening ride on the first day and a morning ride on the second with a single 24-hour rental.

Cycling Southwest Wisconsin has a list of 28 loop rides with something for “every level of bicyclist” with loop lengths from 18 to 70 miles. We’re focusing on rides around Madison ranging from 7 to 19 miles, primarily on bike paths. We’ve come up with five uniquely distinct loop rides that can be mixed and matched in any number of ways.

Popular Madison Bike Loops:

• Monona Bay Loop (7.2 mi)
• Lake Wingra Loop (11.1 mi)
• Lake Monona Bike Loop (12.4 miles)
• Capital City Loop (19.4 miles)
• Lower Yahara River Trail (9 bonus miles)

Monona Bay Loop (7.2 mi)

The Monona Bay Loop is a short ride that connects the MBB Southwest Commuter Path with the Capital City Trail. There’s a natural connection on the north end through Brittingham Park and a nearly complete connection on the south end via the beautiful Wingara Creek Trail. The neighborhood gap is through the Monroe Street district, which is very bike-friendly.

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Lake Wingra Loop (11.1 mi)

Everybody talks about the Monona Lake Loop, but there’s a Lake Wingra Loop, too. Much like its more famous cousin, there’s some debate about maximizing your time on a trail versus staying as close as possible to the lake. There’s a good argument for going all the way through the arboretum and finding a neighborhood connection on the west side. However, we tossed a coin and mapped our ride through the Cannonball Trail to the junction at Velo UnderRound.

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Lake Monona Bike Loop (12.4 miles)

The Lake Monona Bike Loop is a classic Madison bike ride. It follows the Capital City Trail on the west side of the lake and a signed on-road route through the city of Monona. For some reason, there is still debate about “the route.” There are three choices through Atwood – the “official” signed route along the lake, Atwood Ave (meh), or staying on Capital City Trial to Olbrich Botanical Gardens.

We chose the CapCity Trail option because the route finding along the lake was tedious. However, in Monona, we decided to stick with the signed route closest to the lake instead of the shortcut on Winnequah Road. The one thing people absolutely agree on is stopping for ice cream at Monona Bait & Ice Cream Shop on a hot summer day.

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