How to Plan a Group Motorcycle Ride Without Losing Friends

Planning a group motorcycle ride? Whether it's a weekend trip or a multi-day touring adventure, group rides can be the best part of motorcycling—or the most frustrating. In this episode of Best Motorcycle Roads, we share essential group ride planning tips, including how to set expectations, avoid drama, and create epic rides your friends will actually thank you for.

We cover:

- How to plan a group motorcycle ride that works for everyone

- Tips for organizing motorcycle trips with multiple riders

- What gear and tech help group rides run smoother

- Real stories from years of group touring across the Midwest and beyond

Whether you're a ride captain or just trying to survive your next group trip, this episode will help you keep the peace, ride better, and stay connected.

TOOLKIT – RECOMMENDED GEAR & LINKS

These affiliate links help support the podcast (thanks for clicking!).

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Planning your next motorcycle road trip through the Midwest? In this episode of Best Motorcycle Roads, we highlight six of the most motorcycle-friendly towns in the Midwest—destinations that offer stunning rides, rider-welcoming atmospheres, and unforgettable roadside experiences.

We explore towns that go out of their way to welcome bikers—whether it’s a historic downtown with great restaurants, scenic routes perfect for cruising, or parking lots full of chrome on summer weekends.

Towns Covered in This Episode:

• Galena, Illinois – Ride the Stagecoach Trail, explore historic streets, and sip top-tier Bloody Marys

• Marquette, Michigan – Cruise Lake Superior’s shores and grab a warm pasty at a local gem

• Lanesboro, Minnesota – Fall foliage, winding river roads, and cozy breakfast spots

• Hermann, Missouri – Scenic hills, riverside rides, and a bratwurst or two

• LeClaire, Iowa – Ride the river bluffs and stop by the American Pickers HQ

• New Glarus, Wisconsin – Swiss charm, cold beer, and curvy Driftless Region roads

Rider Toolkit Mentioned:

• Kickstand Pad – Park securely on gravel and grass

• Cable Helmet & Jacket Lock – Secure your gear while you explore

• Microfiber Towel Set – Perfect for cleaning bugs, dew, and helmets

• Mini Jump Starter w/ USB Charging – Save your battery and charge your devices

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If you're planning a long motorcycle trip, this is the gear checklist you didn’t know you needed. In this episode, we break down the motorcycle gear we actually wear on multi-day rides — including modular helmets, rain gear, base layers, boots, and glove strategies that work across weather, miles, and mistakes.

Whether you're doing your first overnight ride or refining your long-haul setup, this guide covers real-world motorcycle gear for comfort, safety, and convenience. No fluff — just trip-tested gear that’s earned its place in our saddlebag.

• Why modular helmets are worth every penny
• Base layers that regulate temp without bulk
• The rain gear system we pack (and how we pack it)
• Smart layering with multiple glove types
• Why latex glove liners are still a favorite
• Boots with protection and walkability
• Eye drops, boot dryers, and the weird little things that save a ride

Some links are affiliate links — if you click and buy, we may earn a small commission at no cost to you.

That helps support the show and keeps the wheels turning. Thanks for your support!

• Bohn Body Armor → https://www.bohnarmor.com/

• Modular Helmet → https://amzn.to/44GeAEV

• Pinlock Visor Insert → https://amzn.to/4dpENcZ

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• Nelson-Rigg Rain Gear → https://amzn.to/43srvrS

• Nitrel Gloves → https://amzn.to/3FmOWKX

• Travel Boot Dryer → https://amzn.to/3SHIm4P

• 6” Riding Boots → https://amzn.to/3Zg2tLp

• Eye Drops → https://amzn.to/3SKKQ2m

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