There’s something much more awesome and intimate about discovering a place from the seat of a bike. Pedaling around the turn to find a secluded stretch of beach, no car engine muffling out the sound of waves crashing against the shore. So it is here in Montauk, Long Island, where two wheels are far better than four. You’ll be surprised by how much you can see without breaking a big sweat or having to wear those unflattering padded shorts.
I. The Bike
Take your Own: If you’ve got your own bike, you’ll probably want to take it with you on the Long Island Railroad. Be advised, there are some strict rules, so be sure to read all regulations (or consult our travel bike guide) before visiting the website to print out your Bicycle Permit Application.
Rent: If your bike is getting fixed or in your home country, no problem. The Montauk Bike Shop on Main St. has rentals available for $10 per hour or $39 per day.
II. Where to Stay
Housed in an iconic American Tudor landmark building, Solé East (90 Second House Road) is located just far enough outside of town to feel like a true oasis. The hotel rents bikes at a low rate to guests, but be sure to reserve one in advance. There are 67 crisp white rooms, seven garden cabana suites, and a lush garden that keeps the pool and surrounding bed-lounges as private as can be. On the property, Backyard serves fresh organic fare and has a fully stocked bar that makes great margaritas to enjoy in a hammock. During the summer, expect live music at night and a weekly poolside DJ on Saturdays. Solé East also offers complimentary pick up from the Long Island Railroad and the Hampton Jitney.
All rides begin at Solé East from the main entrance.
Find other Hotels in the area:
Ride 1: Total Distance: 6 miles. Locals Only—visit a State Park, eat lobster for dinner, and catch a beautiful sunset.
View or Print Montauk Bike Ride 1: Locals Only in a larger map
To get to the park, make a right out of the hotel and take Second House Road. When you get to a sharp curve and 15mph sign, keep going straight (not right) and take the road over the train tracks. As you come down the hill make the left onto Navy Road. Follow the road as it hugs the bay and turns into Hither Woods Preserve Road. You’ll now be in Hither Woods Preserve, which abounds with trails and scenic overlooks.
After your hike, head to Duryea’s Lobster Deck (65 Tuthill Road) for some of the freshest seafood in town. Return to Navy Road and pedal east (don’t cross over the train tracks again) almost to the end—the Sunset Saloon will be on your left, and a tennis court on your right. Cut to the right onto a gravel road that runs parallel to the train tracks. You’ll pass the Shellfish Hatchery as you ride into the train station. When you exit the parking lot make a left and find the road (unmarked Tuthill Road) that heads towards the water—it will look like you’re on the road to nowhere but just trust it. As you come around the corner, Duryea’s will be on your left. Come on the early side to beat the crowds, plus there’s a better place to watch the sunset.
As you exit Duryea’s make a left and bike up the hill. The road will dive downhill and come up just as the Montauket Hotel (88 Firestone Road) appears on your left. Get here in time for the sun to work its magic on the sky. The views are beautiful and the beers are ice cold. A popular spot with tourists and locals alike, don’t be surprised to make new pals who’ll offer to give you and your bike a ride home in their pick-up truck.
Ride 2: Total Distance: 5 miles. The Beach Bum—take in a happening town beach, organic lunch, a sail on the pond, and root beer on tap at dinner.
View or Print Montauk Bike Ride 2: The Beach Bum in a larger map
To get to Nick’s on the Beach (148 S Edison St.), exit the hotel and make a left onto Second House Road. Follow the road as it curves past the red Fort Pond Lodge. When you come to the intersection take S. Dewitt Place and cross Main St. (Montauk Hwy 27) onto Eton Road. The Oceanside Beach Resort will be on your left. When Eton Road ends take a left onto S. Emerson. Ride with the dunes on your right until you come to Nick’s. With its live band and lively crowd (helped by great drink specials) it shouldn’t be hard to miss. Find a good spot for your bike, grab your towel, and head onto the beach. If you’re lucky, the lifeguards on break might ask you to join in on a pickup game of beach volleyball.
For lunch, leave your stuff on the beach and bike (or walk) over to Naturally Good Food and Café (38 S Etna Ave). Head north (away from the beach) on Edison St. and make your second right onto S Etna Ave. Eat in their shady backyard garden or take lunch back to the beach with you, but don’t miss out on the local organic fare. The specials’ board is always worth checking out, but the Bruce, a fresh (as in caught that morning) tuna sandwich with red onion, is the real mainstay. Just make sure to time your trip well as the kitchen closes from 11:00-11:30 daily.
Wind picking up? If you’re leaving from the beach head north on Edison and then make your first left onto S Elmwood Ave. Follow S Elmwood until it ends at Main St. (Montauk Hwy 27) Veer to the left and join the main road for your next stop, the Puff and Putt Family Fun Center (659 Montauk Hwy.), which will be on your right, directly across from the IGA. Puff and Putt has an 18-hole mini-golf course, but it’s really worth going for the boat rentals. Since there’s a breeze, take a sunfish out for a tour of Fort Pond and chill out. If the air is calm, rent a peddle-boat and give your legs a workout.
Need a drink? Leave Puff and Putt, make a right onto Main St. (Montauk Hwy 27) and head west out of town. When the Oceanside Beach Resort is on your left (you can’t miss the bright yellow smiley face on its façade) make the right onto S Dewitt Place and then another right onto Second House Road. You can stop at your room to wash the sand out of your hair before dinner, or head right to the Second House Tavern (161 Second House Road). Keep an eye out for its wooden sign and long driveway on the left, just a few minutes past Solé East. Whether you sit in the dining room or at the bar, you’ll be satisfied with the fresh seafood, homemade mac and cheese, and foamy root beer. After dinner, make a right onto Second House and you’ll be home in no time.
Ride 3: Total Distance: 7 miles.Surf ‘n’ Turf –the perfect hike, surfer’s paradise, and the best drive-in burgers and ice cream.
View or Print Montauk Bike Ride 3: Surf n Turf in a larger map
Leave the hotel and make a left onto Second House Road, heading into town via a left on S Dewitt Place. Ride east on Main St., pass through and out of town. As you leave, St. Therese church will be on your right. Once you get up the hill the free wifi-bearing library will be on your left. Keep an eye out for a right-hand sign that reads Shadmoor State Park (about a quarter mile east of town). Pull over and leave your bike by the entrance. Here you can hike along breathtaking bluffs, through freshwater wetlands, and enjoy birdwatching from elevated platforms. Entrance to the park is free.
Post-hike head to Ditch Plains for a dip in the ocean. Get back on the main road (Montauk Hwy 27) and continue east. Ditch Plains Road will be your first paved road on the right, follow it to the beach. There are three parking lots for Ditch Plains and each one corresponds to a slightly different beach atmosphere. Go to Lot 1 (the first one on your right) if you want to be close to bathrooms. When you enter the beach, head right to eschew the crowds. Go to Lot 2 for the famous Ditch Witch: a concession stand selling everything from quesadillas to lemonade. Go to Lot 3 (the dirt lot) if you want to sunbathe and surf. Fair warning: the beach is smaller here, and if you’re an unfamiliar face or without a board, the locals may wonder why you’re there.
After a day at the beach, return to town via Ditch Plains Road and swing a left onto Montauk Hwy 27 for a burger and shake at John’s Drive-In (695 Montauk Hwy). Located on Main St. you can’t overlook the retro drive-in sign. John’s is a great place to grab an inexpensive dinner, so try the John Burger with special sauce and indulge in the homemade ice cream—it’s as good as it gets.
Ride 4: Total Distance 4 miles. Hampton Nights—tour a historical home, dine in style and rub shoulders with celebrities over caprihinias
View or Print Montauk Bike Ride 4: Hampton Nights in a larger map
When you leave Solé East make a left onto Second House Road and head into town via a left on S Dewitt Place. Instead of riding onto Main St. pull onto the grass on your left, where The Second House Museum (631.668.5340) is hiding behind the hedges. Built in 1797, Second House is the oldest building in Montauk and one cultural experience worth your while; take a tour and explore the lovely grounds for eight bucks.
After the museum, hop on your bike and head to dinner at Harvest on Fort Pond (11 S Emery). Make a left onto Main St., then take your first left onto S Emery. Easily Montauk’s most famous and frequented restaurant, sit outside in the beautiful herb garden where sunflowers tower overhead. If there’s a wait, order a mojito—the mint is picked from the garden each night—and take a stroll on the private dock overlooking the pond. Famous for its Mediterranean-influenced family-style dishes and expansive wine list, nothing is a miss on this menu, but the Seafood Brushcetta and Whole Red Snapper are particularly good.
After dinner, you’ll be happy to have your bike when you see the parking (or lack thereof) at The Surf Lodge (183 Edgemere St). Leave the Harvest by heading east on S Euclid Ave (running parallel to Main St). Make the second left onto Edgemere St (County Rte 49) and head north. Stay on Edgemere until The Surf Lodge appears on your left. Grab a drink from the inside bar before joining the famous faces outside. Check the website for a full schedule of live music and movie screenings. When you’re ready to head home, make a left out of the parking lot and your first left onto Industrial Road. Follow Industrial over the train tracks and as it winds to the left and turns into Second House Road.
All these spots are within close proximity so be sure to mix and match and create your perfect itinerary!
How to get to Montauk from NYC
Montauk is easily accessible by rail and road. The Long Island Railroad offers daily trains to and from Penn Station. Check out MTA for a full schedule. Two tips: Be prepared for crowds on the weekend and pack a sweatshirt for the relentless air conditioning. The Hampton Jitney also offers daily service to the east end and departs from various locations in Manhattan and Brooklyn. Check out hamptonjitney.com for a full schedule and be sure to make a reservation. Check out the Chamber of Commerce at www.MontaukChamber.com for more information.
Photo: Chris barker
Sarah Knapp is a Brooklyn based entrepreneur whose love for the outdoors and community building led her to the October 2013 creation of OutdoorFest. She has a BA in History, is a Wilderness First Responder and a NY state hiking, camp and boating guide. Her proudest achievement to date is reading the Aeneid in Latin. 
Allison was one of our first top writers and Chief Editor but is no longer working with offMetro. Allison is a native New Yorker, who has lived in Rome, Tuscany, Melbourne, Toronto and Los Angeles. She frequently contributed travel pieces to Family Travel Forum, using her own children as guinea pigs as they travel the globe. She never missed a chance to sample local delicacies, as her love for travel goes hand-in-hand with her love for food and wine. 
Josh Laskin is a freelance travel writer and photographer based in the White Mountains of New Hampshire. When he is not at work or on the road, you can find him in the mountains snowboarding, climbing, hiking, fly fishing, mountain biking, and eating bagel bites.
Annie is a travel writer, environmentalist, and surfer based in Venice, CA. She heads up our West Coast team, keeps our grammatical errors in check, and makes sure our California writers always have a plan for their next adventure. Follow Annie’s travels @annelisemcb.
Carly Pifer is a freelance writer who has been known to follow whims inspired by romantic movie scenes or colorful street style shots to India, Japan, Tunisia and Argentina. After stints living in Seoul, Boston, Paris and Los Angeles, writing and searching for something intangible, she landed somewhat steadily in Brooklyn and has begun to find inspiration in her more immediate surroundings. 
Kate E. O’Hara is a New York based freelance writer and photographer who loves all things food—especially the people who make it and market it. Her writing aims to capture the essence of the food experience; the stories that go well beyond a plate of ingredients. In addition to her love of food, Kate is also known to have a hankering for red wine and craft beer. You can also find Kate on Instagram