MobiriseBe sure to download and read the GPS User Guide to correctly set your GPS to use these routes.
For individual routes:
Click on the MAP link of each route to see a complete map
Click on the GPX link of each route to download the GPS route file
Click on the PDF link of each route to view/download the PDF printable route file
If you want to use your phone as a GPS, download the OsmAnd+ app and follow the tutorial HERE
(Do not use ZIP versions if there are last minute route changes- individual routes will be most up-to-date)
Note: To download ZIP files, right-click or control-click the links. Otherwise you may get a 404 error.
All Routes GPX format (As of 06/08)
For 2026 forward, our GPX route files will only contain a single TRIP PLANNER version. These routes use mostly shaping points for compatibility with Garmin zumo XT, XT2, 390 and 590 series, as well as BMW Nav5, Nav6 and all Garmin GPS units that use the Trip Planner App to access routes. These routes also work well with TomTOM and phone apps.
MAP GPX
RouteType: DESTINATION – Scenic rural Indiana loop through small towns and countryside visiting four covered bridges. Touring-bike friendly with mix of sweepers and straight sections.
Navigation difficulty: AVERAGE – Several county roads and turns but follows a logical clockwise loop.
Distance: 156 miles
Lunch Stop: Several options in Brownstown, IN.
Direction from Madison: WEST, CLOCKWISE
Comments: Scenic ride with farmland views, light traffic, and a mix of curves and flat stretches. Opportunities for photos at historic covered bridge sites.
MAP GPX
RouteType: DESTINATION – Scenic touring loop through southern Indiana with optional stops at five covered bridges. Excellent for sport-touring.
Navigation difficulty: AVERAGE
Distance: 237 miles
Lunch Stop: Gnaw Mart in Gnaw Bone, IN. This is a gas station but serves food, well known for their breaded tenderloin sandwich. If this doesn’t suit you, a short detour into Nashville, IN will provide numerous options for lunch.
Direction from Madison: NORTHWEST, CLOCKWISE
Comments: This is a great mix of sweeping state routes and tighter county road sections. Scenic farmland between Madison and Scottsburg transitions to wooded hills near Vallonia and Medora. Nashville offers a charming downtown and is a good midpoint rest stop. The return through Seymour and Commiskey provides easy cruising back to Madison.
Roads are all paved but expect some narrow and curvy sections near Vallonia and Medora.
MAP GPX
RouteType: TWISTY – West from Madison to Shoals, IN, then back. Touring-bike friendly with a good mix of state highways and rural sections.
Navigation difficulty: EASY to AVERAGE
Distance: 216 miles
Lunch Stop: Bo Mac’s in Shoals, IN
Direction from Madison: WEST, COUNTERCLOCKWISE
Comments: This route heads west from Madison into the heart of southern Indiana. Expect a scenic mix of flat farmland near Madison transitioning into rolling hills approaching Shoals. Shoals is a classic southern Indiana town and makes a good halfway break before heading back.
Road surfaces are mostly good, with light to moderate traffic. Expect some faster highway sections balanced by relaxing, scenic rural stretches. Ideal for riders looking for a full-day cruise with plenty of time in the saddle.
MAP GPX
RouteType: DESTINATION, TWISTY – Scenic Kentucky loop south from Madison to the Buffalo Trace Distillery in Frankfort, KY. Perfect for a relaxed day ride with a mix of highway and backroads.
Navigation difficulty: AVERAGE
Distance: 169 miles
Lunch Stop: Buffalo Trace Distillery, Frankfort, KY – enjoy a distillery tour (must pre book on your own) and visit the gift shop if time allows. There are also restaurants nearby in Frankfort for lunch.
Direction from Madison: SOUTHEAST, CLOCKWISE
Comments: This route is an excellent mix of open country roads and gentle curves, taking you into Kentucky’s bourbon country. The highlight is the Buffalo Trace Distillery, which offers a great stop for riders looking for a unique destination.
The route is generally smooth and bike-friendly, though some rural connectors may have rough pavement or narrow shoulders. Great for a medium-distance day trip with time to explore Frankfort before heading back to Madison.
MAP GPX
RouteType: DESTINATION – Ride north/east from Madison to visit the Ark Encounter in Williamstown, KY. Great for a half-day ride with a memorable stop.
Navigation difficulty: EASY – Follows major highways and well-marked connectors.
Distance: 125 miles
Lunch Stop: Ark Encounter Visitor Center – dining options available onsite and nearby.
Direction from Madison: EAST, MOSTLY CLOCKWISE
Comments: This route is a shorter relaxed ride that’s perfect for a morning or afternoon trip. The main attraction is the full-sized Ark replica in Williamstown – a popular and unique destination. Roads are mostly highway, making this a smoother and faster ride compared to the longer touring loops allowing time to visit the Ark Attractions. Ideal for riders looking for a scenic, easy day trip with a cultural or sightseeing focus rather than a twisty technical ride.
MAP GPX
RouteType: Twisty – Long touring loop east from Madison into northern Kentucky, passing through Falmouth and Brooksville before looping back. Excellent mix of sweeping roads and backcountry riding.
Navigation difficulty: AVERAGE – Multiple route changes through rural Kentucky; GPS recommended.
Distance: 225 miles
Lunch Stop: Howards Place in Falmouth, KY. Other local diners and restaurants are available.
Direction from Madison: SOUTH, EAST, CLOCKWISE (FIGURE EIGHT)
Comments: This is a full-day ride designed for those who want to rack up miles and enjoy plenty of Kentucky backroads. The route takes you through farmland and rolling hills, with scenic views and light traffic. After reaching Falmouth, the ride continues east to Brooksville before heading back west toward Madison. Expect a combination of state routes and winding rural roads — a great mix for touring bikes.
MAP GPX
RouteType: Twisty – Shorter ride designed to enjoy Indiana’s legendary “Serpent of 62” section (IN-62), running along the Ohio River.
Navigation difficulty: EASY
Distance:98 miles
Lunch Stop: Rising Sun, IN – several small-town restaurants near Walnut St for a mid-ride meal or coffee stop.
Direction from Madison: NORTHEAST, CLOCKWISE
Comments: A must-do route for twisty-road fans. Indiana 62 between Madison and Rising Sun is locally called the “Serpent” thanks to its tight curves and river views. The road is well-paved but demands attention with its many blind corners and elevation changes. Great for riders looking for a shorter, highly technical ride close to Madison.
MAP GPX
RouteType: DESTINATION – Cross-state loop combining Indiana’s Ohio River roads with a ferry crossing to Kentucky, then returning via Rabbit Hash and back to Madison. Perfect mix of riverside curves, small towns, and a unique ferry ride.
Navigation difficulty: AVERAGE – Two-stage route with ferry timing to consider. Mostly follows river roads with a few key turns. Ferry runs Noon – 10 PM Friday & Saturday, $5.99 crossing fee.
Distance: 177 miles
Lunch Stop: Rabbit Hash, KY – grab a bite at the historic General Store or nearby spots after the ferry crossing. Rising Sun, IN, is another good place for lunch before the ferry.
Direction from Madison: EAST, CROSSING TO KY, COUNTERCLOCKWISE
Comments: This route is a rider favorite thanks to its mix of elements: scenic river roads on the Indiana side, a ferry crossing at Rising Sun to Rabbit Hash, and a fun Kentucky backroad return. The ferry adds a unique experience — check operating hours in advance to avoid delays. Expect a blend of sweeping curves, tight riverside turns, and rural stretches with light traffic. This is a medium-length ride that feels adventurous thanks to the cross-river element.
MAP GPX
RouteType: Sweeping – Long touring loop south from Madison into Kentucky, with Harrodsburg as the primary destination. Excellent for a full-day ride exploring central Kentucky.
Navigation difficulty: AVERAGE – Primarily state highways with some connector roads.
Distance: 244 miles
Lunch Stop: Downtown Harrodsburg, KY – historic area with multiple diners and cafes for a mid-ride break.
Direction from Madison: SOUTHEAST, COUNTERCLOCKWISE
Comments: This is one of the longer Kentucky routes, taking you deep into horse country and through rolling farmland. Harrodsburg, Kentucky’s oldest city, makes a great lunch stop with a chance to stretch your legs and explore a bit. Expect smooth pavement and a mix of sweeping highways and quieter rural sections. A great choice for riders looking for a relaxed touring pace and plenty of seat time. FUEL UP IN HARRODSBURG!!! THERE IS NO FUEL ON ROUTE FROM HARRODSBURG TO CARROLLTON WHICH IS 120 MILES.
MAP GPX
RouteType: Twisty – Epic Kentucky loop from Madison through Owenton, Flemingsburg, Germantown, and Falmouth before looping back. Ideal for riders seeking a long, scenic touring day.
Navigation difficulty: AVERAGE to ADVANCED – Several changes across state and county roads. GPS or pre-loaded route strongly recommended.
Distance: 271 miles
Lunch Stop: Flemingsburg, KY – good choice of diners and small restaurants along Elizaville Ave.
Direction from Madison: SOUTH, EAST, COUNTERCLOCKWISE
Comments: This is one of the longest and most scenic Kentucky loops. You’ll start by heading south toward Owenton, then east into the rolling hills near Flemingsburg — a perfect spot for a lunch break. From there, the route winds through Germantown and Falmouth before heading back toward Madison.
Expect a mix of smooth sweepers, tighter curves, and a few elevation changes. Roads are generally in good shape but may be narrow in rural stretches. This is a full-day ride, so start early and plan fuel stops accordingly. FUEL IS LIMITED BETWEEN CYNTHIANA AND FALMOUTH FUEL STOPS, FUEL UP IN CYNTHIANA!!!
MAP GPX
RouteType: DESTINATION – Scenic loop from Madison to Rabbit Hash, KY, continuing east toward Butler before looping back. Combines riverside roads, small towns, and rolling farmland.
Navigation difficulty: AVERAGE – Multiple rural road transitions, but mostly well-marked highways.
Distance: 158 miles
Lunch Stop: Rabbit Hash, KY – enjoy the historic General Store, grab a snack, and soak in the small-town riverfront charm. Butler, KY, also offers a good secondary stop if riding later into the day.
Direction from Madison: EAST → CROSS INTO KY, CLOCKWISE
Comments: This route is ideal for a mid-to-long day ride, offering both the unique Rabbit Hash experience and more open riding toward Butler. Expect river views, mild curves, and relaxed cruising.
A nice balance between destination ride and scenic exploration.
MAP GPX
RouteType: DESTINATION – Long scenic Indiana loop featuring rural backroads, rolling farmland, and the Tulip Trestle area in Greene County before returning north.
Navigation difficulty: EASY–MODERATE – Primarily follows established state and county roads; longer distance but no complex navigation.
Distance: 258 miles
Lunch Stop: Yoho General Store Solsberry, IN
Direction from Madison: NORTHWEST, COUNTERCLOCKWISE, FIGURE-EIGHT
Comments: This is a full-day ride best suited for an early start. Expect a classic Indiana experience with smooth pavement, long flowing stretches, light traffic, and plenty of quiet countryside. The Tulip Trestle area provides a great mid-ride destination and photo stop. Overall, this is a relaxed but lengthy route that rewards steady pacing.
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