Cyclists call a hundred-mile stretch a “century” and consider riding one to be a signal accomplishment, their sport’s equivalent of running a marathon. More than a thousand cyclists race in the Montauk Century each May, but don’t consider it a missed opportunity. Riding to The End is more fun when you can take a friend and stop to eat when you’re hungry. It’s a relatively straight shot down the pancake-flat Montauk Highway, and if you choose a day with the breeze at your back, you’ll sail through one hundred of the most enjoyable miles in the Northeast.
1 It’s a long way, so start early. Before you hop on the LIRR at Penn Station, you’ll need a bicycle pass—$5, available at the ticket window and good for life. Your destination is Babylon. The point is to do a hundred miles—not to fight city traffic in Queens.
2 In Babylon, head south from the station on Deer Park Avenue. Turn left on East Main Street (a.k.a. Route 27A and Montauk Hwy.). There’s a bike shop at 218 East Main (at Willow Street) if you need a last-minute adjustment.
3 Exercise caution in East Islip, where your road, Montauk Highway, crosses the giant Heckscher State Parkway. Just after, merge onto Sunrise Highway (Rte. 27 East), then make a quick right onto Montauk Highway (Suffolk County Rte. 85). In a couple of miles suburbia starts to ease, and you’ll see a sign for the Long Island Maritime Museum, a nice rest spot, a quarter mile down West Avenue in West Sayville. If you flat, Sayville Bike Works is at 75 Main Street.
4 Patchogue doesn’t allow bikers and bladers in its center, and the detour is only a half-mile long, but tricky. (Armchair cyclists, skip ahead to No. 5.) Before getting too far into town, turn right onto River Avenue, following the bike-route signs. Cross the railroad tracks. Make a left onto Division Street, which doglegs onto Baker, then again onto Edwards, and then a final dogleg onto Liberty—after all that, you should still be heading east, but only for a few blocks. When Liberty T’s into Grove, turn left and then take the first right: Sweezy Street. When Sweezy T’s, take a left on Roe, then a right onto South Country Road (Rte. 36). Take this shady old road for about ten miles until it links back up with Montauk Highway, now Suffolk County Rte. 80, near Brookhaven.
5 Stay with the Montauk Highway—whizzing past weekend traffic jams for the next six miles. You’re running close to the water, and can smell it in the air. In Moriches, the gateway to the Hamptons, you’ll pass the Moriches Bay Diner. (Pancake lovers, rejoice!)
6 To avoid Southampton’s busy downtown, turn left on Windmill Lane, and then make a quick right onto the brand-new Nugent Street bike lane, which merges back onto Montauk Highway (27 East) after four miles.
7 Sick of Power Bars by now, right? You’ve got options in Amagansett: fried clams at the Clam Bar (2025 Montauk Hwy.), lobster rolls at Lunch (1980 Montauk Hwy.), and tasty fish tacos at La Fondita (74 Montauk Highway). Scarf them all; you’ve already burned it.
8 After clocking another eight miles, bear right onto twisty, rolling Old Montauk Highway. Take this road along the beach into the town of Montauk. It’s four lovely miles until you see the signs for the LIRR station on your left. You can go home now, bragging rights intact, but if you have the legs, press on to the lighthouse, six miles and a few real hills down the road. After all, you didn’t come this far not to go all the way.
9 Now go for a swim.
You’ve earned it.