40 miles of limestone trail, one legendary trailhead town, and views that’ll stop you mid-pedal.

Wisconsin has no shortage of beautiful trails, but the Military Ridge State Trail is something different. Winding 40 miles through the rolling hills, open prairies, and quiet farmland of the Driftless Region, it connects Dodgeville to the edge of Madison along a historic corridor that was once a military road, then a railroad, and now one of the most beloved multi-use trails in the state.

And right at the heart of it (roughly halfway between the western terminus and the Madison suburbs) sits Mount Horeb. With a trail access point right in town, a walkable downtown full of places to eat and explore, and the kind of slow-down energy that makes a bike trip feel like a real getaway, Mount Horeb has become the natural hub for anyone biking the Military Ridge.

Whether you’re planning a quick out-and-back, a full end-to-end adventure, or a weekend trip that leaves room for a post-ride cider and troll-spotting on the Trollway, this guide covers everything you need.

Military Ridge State Trail: At a Glance

Detail	Info
Trail Length	40 miles (Dodgeville to Fitchburg/Madison)
Surface	Crushed limestone (majority); paved asphalt between Verona and Fitchburg
Difficulty	Easy to moderate; 2–5% grade on former rail bed
Best For	Road bikes, hybrid bikes, and gravel bikes (dry conditions)
Trail Pass	$5/day or $25/annual (required for cyclists age 16+)
Dogs	Welcome — must be on leash
Season	Open year-round; best biking late spring through fall
Mount Horeb Trailhead	Located at the historic train depot in downtown Mount Horeb (116 S. Second St., Mount Horeb, WI)

A Little History (Worth Knowing)

The Military Ridge Trail gets its name from a real military road, one of Wisconsin’s first, built in 1835 by soldiers connecting frontier forts. The ridge itself is a geological feature stretching 100 miles toward the Mississippi River, and for centuries it served as a natural transportation route: first by Native Americans on foot, then by pioneer wagons, then by the Chicago and North Western Railway.

That railroad legacy is what makes biking it so pleasant today. Rail-to-trail conversions inherit the gentle grades railroads required (here, a smooth 2–5%) meaning even riders who haven’t been on a bike since summer camp can handle the terrain without feeling like they’re training for a race.

Trail Surface & Conditions: What to Know Before You Go

Most of the trail is surfaced with crushed limestone, which rides comfortably on hybrid or gravel bikes in dry conditions. A 2.5-mile paved asphalt section runs between Verona and Fitchburg on the eastern end (ideal for road bikes).

Heads up: Some sections between Ridgeway and Mount Horeb can develop ruts and loose gravel, especially after rain. If you’re on a road bike, dry conditions are a must for the limestone portions. Hybrid bikes are the most versatile option for the full trail.

A State Trail Pass is required for cyclists age 16 and older. Passes are $5/day or $25/year and can be purchased at DNR offices or self-registration stations along the trail. In Mount Horeb, you can purchase a trail pass at the following locations:

•  Miller’s & Sons Supermarket  608-437-3081
• Mt. Horeb Chamber of Commerce 608-437-5914
• Premier Co-op Mini Mart 608-437-5536
• Trail This Bike Shop 608-274-8447

Trail Segments: Plan Your Ride

You don’t have to do all 40 miles to have an incredible day on the Military Ridge. Here’s a breakdown of the four main segments (plus ideas for how to make the most of each).

Segment	Distance	Highlights
Dodgeville → Blue Mounds	~14 miles one-way	Governor Dodge State Park, big sky ridge views, pastoral farmland
Blue Mounds → Mount Horeb	~8 miles one-way	Cave of the Mounds proximity, rolling Driftless terrain, Blue Mound State Park access
Mount Horeb → Verona	~11 miles one-way	Open prairie, Sugar River wetlands, charming small-town stops
Verona → Fitchburg/Madison	~7 miles one-way	Paved section, connects to Capital City Trail and Madison bike network

Best Shorter Rides

• Mount Horeb to Riley and back (~13 miles round trip): a satisfying half-day ride with open prairie scenery and easy terrain
• Mount Horeb to Blue Mounds and back (~12 miles round trip): rolling landscape, great views, and a stop at Cave of the Mounds on the return
• Dodgeville to Blue Mounds (~19 miles one-way, shuttle back): the most dramatic western scenery with big ridge views

Why Mount Horeb Is the Perfect Trailhead Town

A lot of trails pass through towns. The Military Ridge passes through Mount Horeb and that’s a different thing entirely.

The Mount Horeb trailhead is located at the old train depot (116 S. Second St.)… a fitting starting point, given that the trail itself follows a former rail corridor. The depot sits right next to Brix Cider, which means you can clock in your miles knowing a cold glass of locally made cider is waiting for you at the finish line. From there, it’s a short spin or an easy walk into downtown, where hand-made trolls line the Trollway (that’s what locals call the main street) and the shops, restaurants, and cafes are the kind that make you forget you were planning to keep riding.

Fuel Up Before or After Your Ride

• Driftless Chocolates: artisan chocolate made locally; ideal for packing snacks or rewarding yourself post-ride
• Sjolinds Chocolate House: Norwegian-inspired cafe with pastries and coffee
• MoHo Joes: laid-back spot for a post-ride meal
• Brix Cider: locally made cider; a great way to end a long trail day
• Botham Vineyards: just outside of town; worth a visit if you’re extending the trip

Explore While You’re Here

Give yourself time to wander. Mount Horeb has dozens of hand-made troll sculptures (yes, dozens!) placed throughout downtown and the surrounding area. It’s become as much a destination as the trail itself, and families especially love the troll hunt. The downtown also features independently owned shops, art galleries, and the kind of local character that national chains can’t replicate.

Beyond the Trail: What’s Nearby

The Military Ridge Trail connects to some of the best outdoor and cultural destinations in southwest Wisconsin. A few worth planning around:

• Cave of the Mounds (Blue Mounds): a National Natural Landmark with stunning underground formations; just off the trail near Blue Mounds
• Blue Mound State Park: the highest point in southern Wisconsin at 1,716 feet; access via a spur trail off the Military Ridge
• Governor Dodge State Park (near Dodgeville): camping, swimming, and mountain biking trails; ideal for overnight trail trips
• Ice Age National Scenic Trail: crosses the Military Ridge near Verona, offering a connection to one of the most distinctive hiking routes in the country
• Capital City Trail (Madison): the eastern connection point opens up Madison’s entire urban trail network

Best Times to Ride

The trail is open year-round, but biking conditions vary. Here’s a quick seasonal breakdown:

• Spring (April–May): Trail biking season opens; wildflowers emerge along the corridor; can be muddy after heavy rain
• Summer (June–August): Peak season; best conditions; book lodging in advance if visiting on weekends
• Fall (September–October): The best-kept secret on the trail…fall color on the Military Ridge is stunning, especially through the forested sections near Blue Mounds
• Winter: Snowmobiles permitted on the limestone section; not recommended for cyclists

Practical Tips for a Great Ride

• Bring a hybrid or gravel bike for the full trail; road bikes work well on the eastern paved section
• Carry more water than you think you need — water access between towns is limited
• Download an offline map before you go; cell service can be spotty in the rural sections
• Start early on summer weekends to beat the heat and get a good parking spot
• Check Wisconsin DNR trail conditions before heading out after rain
• Locks are optional but recommended if you’re planning to stop in town

Make a Weekend of It: Stay in Mount Horeb

Here’s the thing about the Military Ridge Trail: the people who enjoy it most are the ones who don’t rush. A single day gives you a great ride. A full weekend gives you the ride plus trolls, local restaurants, a glass of cider on a patio, and the kind of slow morning that reminds you why you took time off in the first place.

Mount Horeb has lodging options for every type of traveler, from full-service hotel to charming inn to vacation rentals with a backyard, and they all put you within easy reach of the trailhead. Guests who stay overnight can fit in two trail segments, see more of downtown, and visit attractions like Cave of the Mounds without feeling rushed.

Tip: Mount Horeb is just 30 minutes from Madison, which means it’s the perfect reason to skip the city hotel and book somewhere with actual character. Visit trollway.com/lodging to see current options.

Ready to Ride?

The Military Ridge State Trail is one of Wisconsin’s genuinely great outdoor experiences and Mount Horeb is its best-kept midpoint. Whether you’re building a full-day ride, a family weekend, or a solo adventure through the Driftless Region, start here.

Plan your visit at trollway.com