5 City-to-City Bike Rides Around the U.S.

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5 City-to-City Bike Rides Around the U.S.

Cycling training can be grueling — it’s either uncomfortable now or uncomfortable later. Cyclists have to accept a certain degree of pain. That’s why there’s the old saying: It doesn’t get easier, you get stronger. A great way to deal with the physical discomfort is to add mental stimulation, so instead of riding that same old loop again, get a group together and plan a city-to-city ride this summer.  We’ve got a few bike trek ideas to get you started:

DIY RIDES (WITH AMTRAK TRAIN RETURN)

CHICAGO TO MILWAUKEE
95 miles  

Flat with occasional wind, this route is bookended with the picturesque skylines of Chicago and Milwaukee, dotted with charming small towns and anchored by awe-inspiring glimpses of Lake Michigan. A bike trail takes you out of Chicago until country roads emerge as you approach the Wisconsin state line. Milwaukee is a city of bridges and waterways with fantastic bike infrastructure.


READ MORE > PREPPING TIPS FOR YOUR FIRST BIKEPACKING ADVENTURE


LOS ANGELES TO SANTA BARBARA
105 miles

Cycling takes on new meaning in California. The air, the water, the mountains, the camaraderie (there so many cyclists) — California has it all.  Expect some inclines and a decent amount of wind on this south-to-north trip. Personally, I’ve never felt a tailwind in California, but I hear they exist.

BOSTON TO PORTLAND, MAINE
120 miles

With this route, you can cover three states in one day! Traffic-wary cyclists can avoid Boston congestion by taking a commuter train out of the city. Urban streets give way to pristine country roads and gorgeous views of the Atlantic Ocean. This route goes through small-town America including Salem and Newburyport, Massachusetts, as well as Portsmouth, New Hampshire. The final few miles into Portland reveals an awesome skyline as you cross the Veterans Memorial Bridge. After a night in Portland, consider heading north to Brunswick.

ORGANIZED RIDES

MIAMI TO KEY LARGO TO KEY WEST
Everglades Bike Club offers an organized ride December 2-5, 2017
Approximately 65 miles (to Key Largo) and roughly 99 miles (to Key West)

Traveling north to south, a tailwind aids in your progression toward Key West. It won’t make riding an 18-mile stretch along the Everglades any easier — nor will it help with the trek across the Seven Mile Bridge — but if you’re prepared to pedal feverishly, you’ll be rewarded with spectacular views.


READ MORE > HOW TO TRAIN FOR MULTI-DAY EVENTS AND CHARITY RIDES


NYC TO MONTAUK
Ride to Montauk offers an organized ride in May
150 miles, with shorter routes available

This ride offers a flat route, good food, lots of company — and organizers even bring your bike back to NYC for you. No matter the distance, you can still participate in the end-of-ride feast and party. Farms, scenic greenways, rustic country air and plenty of friends await. Rest stops, bike repair and support are all included. The lighthouse awaits!

Do you have a favorite point-to-point route? Please share in the comments!

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  • James Huey

    Gainesville Florida to St. Augustine Florida is an excellent 85 mile ride. Starting out, there is a rail/trail that takes one all the way to Hawthorne – about 30 miles. Highway 20 has a great shoulder all the way to Palatka. 207 and 206 are very rideable, and take one to Crescent Beach, S of St. Augustine. A1A is workable into the city, or stay at a hotel S of the city.