Nothing conjures up carefree summer days like cycling to the shore with a towel and a good book in a bike basket.
While the pristine beauty of Hamptons beaches on the south fork of Long Island is unmatched, splendid discoveries also await along the quiet back roads north and south of Route 27. From the horse farms of Sagaponack to the vineyards of Bridgehampton to the wetlands of Napeaque, there’s no better way to explore the byways — and to beat the local traffic — than to ride a bicycle. Our exclusive Guide to Biking the Hamptons lays out everything you need to enjoy your summer ride!
Before You Ride
The Hamptons draw big crowds on the weekends, and that means traffic. Follow these tips for a hassle-free ride:
- Avoid Route 27
Although the shoulders are wide, this main artery through the Hamptons is the least scenic and most congested. Wherever possible, ride your bike on roads north and south of the highway.
- Ride to the beach
Although the beaches of the Hamptons are public, access is controlled through seasonal parking permits. Daily parking fees — at limited numbers of beaches that sell them — can be pricey. Riding a bicycle is your super power, speeding you past the traffic backups and onto the sandy shores of the beach of your choice.
- Get an early start
It’s cooler in the morning, roads are quieter and the beaches are more serene.
- Avoid the door zone
There’s on-street parking on the main streets of Hamptons villages, doors may open or cars may pull out unexpectedly. Slow down and watch for brake lights, movement inside cars and other clues that the situation ahead of you may be changing. In certain locales, such as Sag Harbor, cyclists are required to dismount and walk their bicycles on the sidewalks on the main thoroughfare.
- Cross safely
Where possible, cross at an intersection with a traffic light or pedestrian walkway. If you have to cross a main road in the absence of a crosswalk and you feel uncomfortable riding, then dismount, wait for motorists to yield and walk your bike across the street.
- Ride single-file
The roads throughout the Hamptons are in generally good condition, but shoulders on non-major roads range from narrow to nonexistent. For safety, ride in single file. Also let those with whom you share the road know your intentions by signaling turns and making eye contact with drivers approaching intersections.
- Be alert
Watch out for that motorist who’s too busy dialing a cell phone for a restaurant reservation to pay attention to the road.
- Carry lights
Weather at the shore can be changeable, even during daylight when fog can limit visibility. Travel with front and rear lights on your bike or in your bag.
- Lock up
In keeping with a small-town atmosphere, many people leave bikes unlocked on streets and beaches, but why tempt fate? Secure your bike to hang onto that zen feeling at the beach.
- Be courteous
Always give pedestrians the right of way.
Our Favorite Hamptons Bike Rides
Quiet and shaded roads of the Northwest Woods in East Hampton offer a serene antidote to the go-go pace of the Hamptons. One of our favorites is a meandering, 12-mile ride beginning in East Hampton Village and ending at the the marina in Sag Harbor. Although there’s usually little traffic in the Northwest Woods, the roads are narrow, so keep to the side and ride single-file. Pause in Sag Harbor for ice cream, browsing the shops, or viewing the yachts in the harbor. If you want to extend your ride, pedal to North Haven and catch the South Ferry to Shelter Island.
Sag Harbor Favorites
The Hampton’s outpost of Gwyneth Paltrow’s retail popups, featuring beach-ready fashion, accessories, cosmetics and home goods in an airy cottage overlooking the marina.
4 Bay Street
Expertly curated fashion, accessories and decorative objects, all by women-owned brands. 10 percent of profits are donated to women in need.
133 Main St.
This long-time local favorite for organic and natural foods, also features a juice bar and cafe.
Bay and Division Streets
- Sylvester + Company
Coffee bar with baked goods, chocolate and ice cream, plus beautifully designed home furnishings and accessories in the heart of Sag Harbor.
103 Main St.
A scenic and relaxing option for a weekend morning ride is Shelter Island, the 8,000-acre island located between the North and South Forks of Eastern Long Island. A $6 round-trip ticket on the South Ferry at North Haven gets you and your bike to this historic summer sailing haven where tree-shaded roads unspool to reveal nature preserves, stately waterfront homes and quaint hamlets. The Ram Island leg of this ride is hilly, so skip it if you want a shorter, more leisurely ride. But if you’re feeling extra-ambitious, the ferry at the northerly end of the Shelter Island is the jumping-off point for the North Fork of Long Island, another great locale to explore on two wheels.
Shelter Island Favorites:
- Marie Eiffel
Beach-ready, breezy summer dresses, scarves and accessories.
8 Grand Avenue
- Marika’s Antiques
A treasure trove of antique and retro-modern furniture, lighting and accessories displayed indoors and on the lawn.
6 South Ferry Road
- Sunset Beach
Andre Balázs’s French beach-side restaurant, bar and hotel.
35 Shore Road (closed for 2020)
East Hampton to Montauk Point
For more of a challenge, the 40-mile, out-and-back ride from East Hampton through Amagansett to historic Montauk Point is a favorite among weekend cyclists. Although the Hamptons are mostly flat, a couple of hills await on this ride, so a hybrid or road bike with some gearing options is the best choice. Before you head to the Montauk Lighthouse, the eastern-most point of Long Island’s south fork, pause in the village. Traditionally known for fishing and surfing, Montauk is becoming an increasingly hip destination with enticing boutique hotels, shops and restaurants.
Amagansett and Montauk Favorites:
- Clam Bar
A classic summertime favorite for crisp fried clams and lobster rolls under umbrellas along the highway.
2025 Montauk Highway
- Amagansett Square
Pause at this village green surrounded by fashion and design boutique storefronts, and find refreshment at Jack’s Stir Brew Coffee, Hampton Chutney and Cavaniola’s Gourmet.
- Wyld Blue
Chic fashions for women, including a fine selection of vintage jewelry and accessories. Also check out the selection of sophisticated clothes for children, and beachy home goods.
716 Montauk Highway, Level 2
- Surf Bazaar (Surf Lodge)
Chic and beachy dresses, kaftans, bathing suit cover-ups and bags. Grab a drink on the water-side deck after you shop.
183 S. Edgemere St.
- Sag Harbor Cycle Company offers a schedule of weekly rides, including the popular Saturday Classic.
- Rotations Bicycle Center in Southampton
Tip: Keep a musette bag rolled up in your jersey pocket.
You never know when the bounty of a roadside farm stand will prove too good to pass up.
Summer Cycling Events
Soldier Ride Community Ride for The Hamptons
The Wounded Warrior Project invites you to support and pedal alongside soldiers in this annual Solider Ride.
North Fork Century Ride
Explore the beauty of the North Fork of Long Island along low-traffic, mostly flat country roads. Route options range from 13 to 100 miles with stocked rest stops along the way.
Massapequa Park Bicycle Club Tour of the Hamptons
The tour begins in Southampton and is a mostly flat route taking participants through the south fork of Long Island. 25, 50, 70 and 100 mile routes.
1. Visit a bay beach to rent a stand-up paddleboard.
2. Buy local fish, produce, dairy products and flowers at a weekend farmer’s market.
3. Meet friends for a (insert beverage or small plate) at (insert watering hole).
4. Take the kids to story hour at the library.
5. Explore a local garden or conservancy.
6. Watch a free outdoor concert or film at a park or village square.
7. Haul a surfboard to the shore on a bicycle rack or trailer.
8. Beat the lines at any event where traffic backs up for parking.
9. Take out fried clam rolls from a seafood shop.
10. Sneak off to a matinee just for the air conditioning.
11. Warm up before a yoga class.
12. View osprey nesting on high platforms along wetlands.
Golden Pear Cafes
Southampton, Bridgehampton, East Hampton
With shops all over the Hamptons, coffee, soups, salads, sandwiches and homemade baked goods are always within a short ride.
Springs General Store – Springs
The store has been fancified since the days when an unknown artist named Jackson Pollack traded paintings for groceries. Now, specialty coffees and cupcakes flank the counter where customers order prepared foods and specialties from the grill.
Mary’s Marvelous – East Hampton
Made-from-scratch breakfast and lunch fare includes baked goods, egg dishes, salads, sandwiches and comfort foods. The mini-sandwiches are perfect for a light, on-the-go meal.
Hampton Chutney Co. – Amagansett
Gluten-free South Indian Dosas, made with rice and lentil batter, with a wide array of fresh fillings and accompanied by flavorful chutneys.
Jack’s Stir Brew – Amagansett
Savor their flavorful stir-brewed coffee with baked goods and ice cream rounding out the menu.
Grindstone Coffee and Donuts – Sag Harbor
After your morning ride, snack on baked brioche-style donuts featuring local farm ingredients and flavors.
Main Beach Pavillion – East Hampton
Line up with the beach crowd for simple offerings from the grill, plus ice cream and other sweet treats.
Citarella – East Hampton, Bridgehampton, Southampton
Another off-shoot of a New York City favorite, this gourmet grocery features seafood, a butcher shop, cheeses, prepared foods and baked goods. Stop here to fill your picnic basket.
Harbor Market and Kitchen – Sag Harbor
Fresh, healthy sandwiches, salads and prepared foods, including a yummy breakfast menu. All based on what’s fresh on the East End.
Stars Cafe – Shelter Island
A cozy shop that sells baked goods, coffee and cold beverages, along with some Mexican specialties. Savor your caffeine fix at the tables out front.
Joni’s – Montauk
Yummy smoothies and fresh, healthy wraps with exotic ingredients, plus the cool surfer vibe you’d expect from a shop located two blocks from the ocean.
Laminated, folding Streetwise maps fit easily into your basket or jersey pocket:
- East Hampton
- South Hampton
- North Fork
- Long Island
The ride routes in our guide were created using Map My Ride, a fitness tracking application for GPS-enabled smartphones. Download the app free at this link for pocket navigation and also start recording and sharing your own rides!
Transport Your Bike to the Hamptons
Hampton Jitney & Hampton Ambassador
Long Island Railroad
All you need is a one-time $5 permit to transport your bike by rail. Just note that bicycles are accommodated on a first-come, first-served basis and may be excluded during certain high-volume travel times on the Montauk Branch which serves the Hamptons. Bottom line: Check here for the LIRR’s bicycle policy before you roll to the station on a summer weekend.
Travel between the hamlets of the Hamptons using Suffolk County Transit buses. Each coach is equipped with a front-mounted bike rack. Your bike rides free. Find schedules and more information here.
Prettiest sunset views?
Take an evening ride to Three Mile Harbor (here) or Louse Point. Don’t forget your lights!
624 Montauk Highway
Rent, Buy, Repair
500 Montauk Highway
Rent, Buy, Repair
Piccozzi’s Garage & Bike Shop
Shelter Island Heights
32 Windmill Lane
Rent, Buy, Repair
34 Bay Street
Rent, Buy, Repair
Hotels with Cool Cruiser Fleets
207 Main Street
81 Shore Road (closed for reno)
23 Windmill Lane
183 Edgemere Street
One Bridgehampton – Sag Harbor Tpk.
626 Montauk Highway
Spin classes offer another road to improved fitness. Here’s where to get your indoor cycling fix:
65 Montauk Highway
The Barns at Butter Lane
264 Butter Lane
68 Newtown Lane
760 Montauk Highway