Super looper: a 50-miler that winds through 8 North Shore towns

Ready to test your legs on a half-century? We’ve got the ride for you, with smooth segments for head-down hammering, lots of winding country roads and some really nice scenery along the way.

Like all loops you’re free to jump in anywhere, but we’re suggesting Ipswich center as a starting point for a couple of reasons. Parking is reasonably easy to find and you’ll have some nice options for rewarding yourself at the end of the ride – see More to Explore below.

You’re free to ride the loop counter-clockwise as suggested or to reverse course – it might be a game day call as you assess whether wind is a factor. You’ll enjoy decent riding space on the Routes 1A and 133 sections, and the back road segments are generally in good shape, with a few spots of broken pavement that’ll keep your butt above the saddle.

Traffic is contingent on the day and time of your ride. Generally, summer weekends attract more traffic on the main roads. As a rule, you should find it pretty peaceful on the back roads, regardless of the day.

PRO TIP – Please, please, please do not wear ear buds while riding your bike on the road. Unimpeded hearing is your first line of defense when traffic approaches from behind. I encourage riding with a tail light as well. They are cheap and effective in making your presence known on the road.