1.
New Buffalo Lighthouse loop from Cherry B.
24.5km
01:03
90m
90m
Moderate road ride. Great for any fitness level. Some segments of this route may be unpaved and difficult to ride.
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The best road cycling routes around Three Oaks
By Fede from komoot
·
Updated May 29, 2026
If you've ever tried to plan road cycling around Three Oaks, you know how quickly the options can feel overwhelming. With so many rural roads, orchards, and fields, it's hard to tell which routes are genuinely worth your time and effort, and which are just filler. We get it, and we've been there. That's why we've put together this guide.
Our komoot community has mapped, ridden, and reviewed these routes, saving you the guesswork. This isn't just a recycled highlights reel; it's a curated shortlist of the best road cycling routes around Three Oaks, designed to get you straight to the good stuff. Expect a charming blend of rural roads, open fields, and glimpses of wine country, with terrain that’s generally flat to gently rolling. While you can ride here year-round, the area truly comes alive for cyclists in September, when the annual Apple Cider Century event draws thousands to its scenic routes.
If you only do one ride, make it the New Buffalo Lighthouse – Journeyman Distillery loop from Chikaming Township. At 25.1 miles (40.4 km), it's an easy, rewarding spin that perfectly captures the essence of the region, connecting two iconic local spots. For a slightly longer, more challenging ride that still offers incredible views, we'd point you towards the New Buffalo Lighthouse – Journeyman Distillery loop from Three Oaks Township, a moderate 49.9 miles (80.3 km) route that gives you more time to soak it all in. Ready to roll? Let komoot guide your next adventure.
If you only do 3 of these routes
Compare these routes at a glance
Trail | Distance | Elevation | Difficulty |
|---|---|---|---|
| New Buffalo Lighthouse loop from Cherry B. | 24.5 km | 90 m | Moderate |
| New Buffalo Lighthouse – Journeyman Distillery loop from Chikaming Township | 40.4 km | 140 m | Easy |
| Journeyman Distillery loop from Three Oaks Township | 39.3 km | 120 m | Easy |
| New Buffalo Lighthouse – Journeyman Distillery loop from Three Oaks Township | 80.3 km | 330 m | Moderate |
| Mount Baldy – New Buffalo Lighthouse loop from Union Pier | 57.8 km | 180 m | Moderate |
| New Buffalo Lighthouse loop from The Merritt Family Preserve | 26.4 km | 100 m | Easy |
| Journeyman Distillery – Warren Dunes loop from Three Oaks Township | 71.3 km | 240 m | Moderate |
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New Buffalo Lighthouse – Journeyman Distillery loop from Chikaming Township
40.4km
01:45
140m
140m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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3.
Journeyman Distillery loop from Three Oaks Township
39.3km
01:45
120m
120m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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4.
New Buffalo Lighthouse – Journeyman Distillery loop from Three Oaks Township
80.3km
03:33
330m
330m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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5.
Mount Baldy – New Buffalo Lighthouse loop from Union Pier
57.8km
02:21
180m
180m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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6.
New Buffalo Lighthouse loop from The Merritt Family Preserve
26.4km
01:14
100m
100m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
View route
7.
Journeyman Distillery – Warren Dunes loop from Three Oaks Township
71.3km
03:12
240m
240m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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Tips from the Community
maniboyflex
June 30, 2025, St. Paul Lutheran Church
Founded in 1876, this historic church at 818 Franklin Street offers welcoming worship services and community programs. They run a Sunday soup kitchen.
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Javi Jaavii
February 12, 2024, New Buffalo Public Beach & Lighthouse
The sunsets from this sandy beach, located next to the iconic lighthouse, are magical. It has a dune area where you can take a boardwalk, climb some steps and enjoy even better views.
1
0
Amy
October 7, 2022, New Buffalo Lighthouse
The first lightkeeper began work here in 1840. But, by 1859, the government shut the light which was eventually lost to erosion. The light you see today is a replica that has stood as the same spot by Buffalo Beach since the beginning of the 20th century.
2
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Amy
October 4, 2022, Mount Baldy
Mount Baldy is not technically a mountain, but a 126-feet (38.4 m) shifting sand dune which moves every year. North of the mount, there's a swimming beach which is part of the Indiana Dunes National Park.
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0
Marika Abbà
August 1, 2022, Lake shores
A walk along the shores of the lake is all you need to recharge your energy.
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Frequently Asked Questions
What kind of terrain can I expect on road cycling routes around Three Oaks?
Road cycling around Three Oaks features generally flat to gently rolling terrain, characterized by rural roads and open fields. The modest elevation changes make it suitable for various fitness levels, offering a mix of scenic views.
Are there many easy road cycling routes for beginners in Three Oaks?
Yes, Three Oaks offers several easy road cycling routes perfect for beginners. For instance, the New Buffalo Lighthouse – New Buffalo Lighthouse loop from Chikaming Township is an easy 26.4 km ride, and the New Buffalo Lighthouse – Journeyman Distillery loop from Chikaming Township is another easy option at 40.4 km.
Can I find longer road cycling routes in the Three Oaks area?
For those seeking a longer ride, the New Buffalo Lighthouse – Journeyman Distillery loop from Three Oaks Township covers approximately 80.3 km and is rated as moderate, providing a more extended cycling experience through the region.
Are there any circular road cycling routes available?
Many of the road cycling routes in Three Oaks are designed as loops. Examples include the Journeyman Distillery loop from Three Oaks Township, which is a 39.4 km circular trail, and the Mount Baldy – New Buffalo Lighthouse loop from Gorden Beach Inn, a 57.3 km moderate loop.
What attractions can I see along the road cycling routes in Three Oaks?
Road cycling routes often pass by or near interesting landmarks. You can cycle towards the New Buffalo Lighthouse, or explore areas like the Chikaming Township Park and Preserve. Some routes also offer views of the New Buffalo Public Beach.
What do other road cyclists think about the routes in Three Oaks?
The road cycling routes in Three Oaks are highly regarded by the komoot community, holding an average rating of 4.6 stars from over 6 reviews. Cyclists often praise the scenic rural roads and the accessible nature of the terrain.
Is Three Oaks a good destination for family-friendly road cycling?
Given the generally flat to gently rolling terrain and the presence of several easy routes, Three Oaks is well-suited for family-friendly road cycling. The rural roads offer a pleasant environment away from heavy traffic, making it enjoyable for various ages and skill levels.
What is the best time of year for road biking in Three Oaks?
The best time for road biking in Three Oaks is typically during the spring, summer, and fall months when the weather is mild and the scenery is vibrant. The open fields and rural roads are particularly enjoyable under clear skies.
Are there any specific considerations for winter road cycling in Three Oaks?
Winter road cycling in Three Oaks can be challenging due to colder temperatures and potential for snow or ice on rural roads. It's advisable to check local weather and road conditions before heading out and to ensure your bike is equipped for winter riding.
Where can I find parking for road cycling routes in Three Oaks?
Parking availability varies by route starting point. Many routes begin from or pass through townships like Three Oaks Township or Chikaming Township, where public parking options may be available. It's recommended to check specific route details for designated parking areas.
How many road cycling routes are available in the Three Oaks area?
There are over 10 road cycling routes documented in the Three Oaks area on komoot, offering a variety of distances and difficulty levels for cyclists to explore.
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