Cruiser Rally Route 66: Your Essential Beginner Guide

Cruiser Rally Route 66 for beginners: Plan your epic motorcycle journey on America’s most iconic road with this easy-to-follow guide. Discover essential tips for route planning, bike prep, safety, and enjoying the ride of a lifetime.

Riding a motorcycle along Route 66 is a dream for many. Known as the “Main Street of America,” this historic highway promises adventure, nostalgia, and stunning scenery. But if you’re new to long-distance motorcycle rallies, the idea of tackling Route 66 can feel a bit daunting. Where do you even start? Don’t worry, friend! We’re going to break down everything you need to know to make your Route 66 cruiser rally a smooth, safe, and unforgettable experience. We’ll cover planning your route, getting your bike ready, staying safe, and soaking in all the history.

Why Route 66 for Your First Cruiser Rally?

Route 66 isn’t just a road; it’s a legend on two wheels. For beginner riders looking to experience a true motorcycle adventure, it’s an excellent choice. Here’s why:

Well-trodden Path: Millions have ridden Route 66, meaning services, accommodations, and fellow riders are abundant. You’re rarely truly alone.
Rich History & Culture: Every mile is packed with Americana – classic diners, quirky roadside attractions, and historical markers. It’s a rolling museum.
Varied Scenery: From the bustling cityscapes of Chicago to the vast deserts of Arizona and the Pacific coast, Route 66 offers diverse and captivating views.
Supportive Community: The biker community often embraces Route 66 rides. You’ll find camaraderie and a shared passion for the journey.
Manageable Length (Relatively): While long, its defined start and end points make it easier to plan and navigate than open-ended routes.

East to West (Chicago to Santa Monica):
Pros: The weather generally gets better as you head west, particularly avoiding the potentially harsh winter conditions in the Midwest early in your trip. You’ll face the prevailing winds mostly from behind. Many iconic Route 66 sights are more easily accessed heading west.
Cons: You might encounter more traffic as you get closer to California.

West to East (Santa Monica to Chicago):
Pros: You can experience the California coast first.
Cons: You might face more headwinds, and the weather in Illinois and Missouri can be unpredictable earlier in biking season.

The Absolute Minimum (Rushed): 10-14 days. This will be a fast-paced trip, hitting the highlights and doing a lot of riding each day. Not recommended for beginners wanting to truly experience it.
Recommended (Comfortable Pace): 3-4 weeks. This allows for more leisurely days, time to explore attractions, rest days, and spontaneous stops. You can cover significant ground without feeling exhausted.
The “Full Experience”: 4-6 weeks or more. This lets you really dig deep, explore detours, revisit favorite spots, and truly immerse yourself in the journey.

For your first cruiser rally, aim for at least 3 weeks. This provides a good balance between covering the route and actually enjoying the experience and your motorcycle.

Mapping Your Course: The Real Route 66

Route 66 isn’t one continuous, perfectly paved road anymore. It’s been bypassed by Interstates in many sections. You’ll be riding a patchwork of original alignments, some newly preserved stretches, and sections that run parallel to modern highways.

Navigation Tools:
Dedicated Route 66 Apps & Websites: Several resources are designed specifically for Route 66 travelers. They highlight original alignments, attractions, and lodging. Search for “Route 66 GPS maps” or “Route 66 navigation apps.”
GPS Devices: A rugged GPS unit (like Garmin Zumo or TomTom Rider) is invaluable. Make sure it’s updated and pre-loaded with your route.
Paper Maps/Atlas: Don’t underestimate good old paper maps! They are a fantastic backup if electronics fail and allow for a broader overview of your trip. A good motorcycle atlas or dedicated Route 66 road atlas is a must.
Google Maps/Other Navigation Apps: Can be used, but be specific. They might default to the fastest route (Interstate) unless you manually direct them. Look for the “avoid highways” option, but be aware this might sometimes lead you down unpaved roads if not carefully monitored.

Classic Motels: Many historic motels still operate and offer an authentic Route 66 experience.
Chain Hotels: Widely available in larger towns and cities for reliable comfort.
Campgrounds: If you enjoy camping, many campgrounds are available along the route.

Tip: For your first rally and to reduce stress, book accommodations a few days in advance, especially in popular areas or during peak season. This ensures you have a place to rest after a long day of riding.

Preparing Your Cruiser for the Road

Your motorcycle is your partner on this journey. Making sure it’s in top shape is crucial for reliability and safety. As your trusted guide, Barry K. Richmond, I can tell you that a little prep goes a long way!

The Essential Pre-Trip Check (The “Barry K. Richmond” Pre-Ride Tune-Up)

This isn’t about rebuilding your engine; it’s about ensuring everything is functioning as it should. Think of it as a thorough physical for your bike.

1. Tires:
Check Pressure: Crucial for handling, tire wear, and fuel efficiency. Consult your owner’s manual for the correct pressure.
Inspect Tread Depth: Look for wear bars or simply check that there’s plenty of tread left. You don’t want to be replacing tires halfway through the rally.
Look for Damage: Check for cuts, bulges, or embedded nails/objects.

2. Brakes:
Pad Thickness: Ensure there’s ample life left in your brake pads.
Fluid Level & Condition: Check the brake fluid reservoir. It should be between the min/max lines. If the fluid looks dark and murky, it’s time for a flush.
Lever Feel: Squeeze the brake levers – they should feel firm, not spongy.

3. Chain & Sprockets (if applicable):
Lubrication: Clean and lube your chain regularly, especially in dusty or wet conditions.
Tension: Check chain tension. It should have a little bit of slack, but not too much. Again, consult your manual.
Wear: Inspect sprockets for hooked teeth – a sign they need replacing.

4. Fluids:
Engine Oil: Check the level and condition. If you’re near an oil change interval, do it before you leave.
Coolant (if liquid-cooled): Ensure the level is correct and the coolant looks clean.

5. Lights & Electrical:
Headlight, Taillight, Brake Lights, Turn Signals: Test all of them. Replace any burnt-out bulbs.
Horn: Make sure it works loud and clear.
Battery: Check connections for corrosion. A weak battery can leave you stranded. If it’s old, consider replacing it.

6. Cables:
Throttle & Clutch Cables: Check for fraying or sticking. Lubricate if necessary.

7. Belts (if applicable):
Inspect for cracks or fraying.

Essential Tools & Spares for the Road

You don’t need to carry a full mechanic’s toolbox, but a few key items can save your ride.

Basic Toolkit Checklist:

Screwdrivers (Phillips and flathead)
Wrench set (metric and/or standard, depending on your bike)
Socket set with ratchet
Pliers (needle-nose and regular)
Adjustable wrench
Tire pressure gauge
Tire repair kit (plugs, sealant, CO2 cartridges or mini-pump)
Duct tape (a rider’s best friend!)
Zip ties
Owner’s manual (digital and/or physical)
Small container of chain lube (for chain-driven bikes)
Gloves (for working on the bike)

Recommended Spares:

Spare fuses
Spare bulbs (headlight, brake light, turn signals)
Spare spark plug(s)
Clutch and throttle cables (if they look questionable)
Small quart of your bike’s specific oil

Luggage: Saddlebags (hard or soft), tank bag, and a tail bag are common choices for cruisers. Distribute weight evenly.
Gear: Never compromise on riding gear. This includes a DOT-approved helmet, armored jacket and pants, gloves, and sturdy boots. Consider rain gear – the weather can change in an instant.
Essentials: Keep important documents (license, registration, insurance, emergency contacts) easily accessible. Include a basic first-aid kit.

Safety First: Riding Route 66 Responsibly

Safety is paramount, especially on a long journey with varying road conditions and traffic.

Be Visible, Be Aware

Bright Gear: Wear brightly colored riding gear and consider reflective elements. You want to be seen!
Headlight On: Always ride with your headlight on, even during the day.
Frequent Scanning: Constantly scan your surroundings – mirrors, beside you, ahead. Anticipate potential hazards.
Road Hazards: Route 66 has older sections. Watch out for:
Uneven pavement and potholes
Gravel or loose debris on road edges
Sudden dips or rise in the road surface
Wildlife crossing
Large trucks and RVs sharing the road

Heat: Stay hydrated! Carry plenty of water. Take breaks in the shade. Be extra cautious in desert areas where heat shimmer can distort your vision.
Rain: Slow down, increase following distance, and avoid sudden maneuvers. Metal surfaces (like manhole covers and painted lines) become extremely slippery.
Wind: Crosswinds can be strong and unpredictable, especially in the Plains states and desert regions. Stay alert and be ready to counteract gusts.

Fatigue Management

Long days on the bike can be exhausting.

Take Breaks: Stop every 1-2 hours to stretch, hydrate, and clear your head.
Listen to Your Body: If you’re feeling tired, pull over and rest. Don’t push yourself. A nap at a scenic overlook can do wonders.
Stay Hydrated and Eat Well: Dehydration and poor nutrition exacerbate fatigue.

Chicago: Begin at the “Begin Route 66” sign on East Adams Street. Explore the city before hitting the road.
Gemini Giant (Wilmington): A classic roadside attraction.
Standard Oil Gas Station (Odell): A perfectly preserved piece of history.

Missouri: The “Show Me” State’s Charm

St. Louis Gateway Arch: An iconic landmark visible from miles around.
Meramec Caverns (Stanton): A vast natural wonder and former Route 66 attraction.
Cuba: Known for its vibrant murals.

Blue Whale of Catoosa: A quirky and beloved photo op.
Cyrus Avery “Mother Road” Plaza (Tulsa): Celebrate the father of Route 66.
Arcadia Round Barn: A unique architectural marvel that still stands.

Texas: The Panhandle’s Wide Open Spaces

Cadillac Ranch (Amarillo): Bring spray paint and leave your mark (responsibly!).
MidPoint Cafe (Adrian): Officially marks the halfway point of Route 66. Famous for its “Ugly Crust Pie.”

New Mexico: The Enchanting Southwest

Tucumcari: Famous for its vintage motels and neon signs.
Santa Fe: A charming detour with historic plazas and art galleries (note: Santa Fe is a detour from the original Route 66 alignment through that area).
Petrified Forest National Park & Painted Desert: Absolutely stunning natural formations.

Winslow, Arizona: “Standin’ on the corner…” – a must-stop for Eagles fans.
Meteor Crater: A spectacular impact site near Winslow.
Grand Canyon National Park: A worthwhile detour that no Route 66 traveler should miss.
Seligman & Kingman: Key towns that helped preserve stretches of Route 66.

Oatman: A quirky old mining town where wild burros roam the streets.
* Santa Monica Pier: The official “End of the Trail.” Celebrate your achievement!

Your Cruiser Rally Route 66: A Beginner’s Checklist Summary

To help you keep track, here’s a quick checklist to ensure you’re set for your Route 66 adventure.

Frequently Asked Questions About Route 66 Cruiser Rallies

As Barry, I get