Nothing conjures up carefree summer days like cycling to the shore on a classic cruiser 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 Sagaponak 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 Hamptons Riding Guide lays out everything you need to enjoy your summer ride!
Transport Your Bike to the Hamptons
Hampton Jitney Bus & 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 in the Hamptons? Take an evening ride to Louse Point in the Springs. Don’t forget your lights!
624 Montauk Highway
36 Gingerbread Lane
2101 Montauk Highway
60 Park Place
725 Montauk Highway
Piccozzi’s Garage & Bike Shop
Shelter Island Heights
716 Main Street
32 Windmill Lane
New! Sag Harbor Cycle Company
34 Bay Street
Hotels with cool cruiser fleets
207 Main Street
81 Shore Road
23 Windmill Lane
183 Edgemere Street
161 Second House Road
Spin classes offer another road to improved fitness. Here’s where to get your indoor cycling fix:
199 Main Street
58 Deerfield Road
65 Montauk Highway
The Barns at Butter Lane
264 Butter Lane
68 Newtown Lane
1. Yakkay 52 Tokyo Flower Complete Helmet, $150 2. Land’s End Bike Picnic Basket, $55 3. Playdate Sweet Jane Bike, $649.99 4. Ryders Empress Sunglasses, $39.99 5. DSquared2 Striped Shorts, $240 6. Crane Riten Rotary Bell, $23.99 7. Basil Bottle Basket, $36 8. Hermès Hippocampe Beach Towel, $550 9. Pret a Surf Chambray Bra and Bloomer 10. Native Miller Rubber Shoes, $44.99
12 Things We Like to Do By Bicycle in the Hamptons
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, Sag Harbor, 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 – Amagansett
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.
Eli’s – Amagansett
The East End outpost of the familiar Manhattan food purveyor is located in an historic farmer’s market. Shop for produce and products that are grown (or raised) on the North and South Forks of Long Island.
Jack’s – Amagansett
Their flavorful stir-brewed coffee is the best in the Hamptons. (In our opinion.) Baked goods and ice cream round out the menu.
Luz’s Deli – Amagansett
It looks like an ordinary deli, but its super power is the empanadas — homemade daily with a variety of savory fillings.
Main Beach Pavillion–
Line up with the beach crowd for simple offerings from the grill, plus ice cream and other sweet treats.
Citarella – East Hampton, Water Mill
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.
Bagel Buoy – Sag Harbor
A popular, nothing-too-fancy weekend stop for bagels, plus sandwiches, omelets and wraps.
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.
Snag a bag of cinnamon-sugar Dreesen’s donuts at Scoop du Jour in East Hampton and pedal to Town Pond with your kids to see the swans.
Laminated, folding Streetwise maps fit easily into your basket or jersey pocket:
- East Hampton
- South Hampton
- North Fork
- Long Island
Available at Bookhampton shops in East Hampton, South Hampton and Sag Harbor or order here.
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!
Before You Ride
The Hamptons draw big crowds on the weekends, and that means traffic. To get the most fun and relaxation out of your ride, follow these tips:
- 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 ($40 at Cooper’s Beach in South Hampton). 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 and 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 a car 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 his 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. Keep 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 coffee and shopping, or, if you want to extend your ride, pedal to North Haven and catch the South Ferry to Shelter Island.
Sag Harbor Favorites
Distinctive apparel and brands for women and men in an airy shop overlooking Sag Harbor’s main thoroughfare.
127 Main Street
This long-time local favorite for organic and natural foods, also features a juice bar and cafe.
Bay and Division Streets
- Ruby Beets Antiques
Vintage and contemporary home furnishings, art, lighting and accessories.
25 Washington St.
- 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:
- Boltax Gallery
Contemporary art gallery featuring the work of emerging and mid-career artist.
21 North Ferry Road
- 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
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. While most of the Hamptons are 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
- Melet Mercantile (no website)
Beach branch of the Soho by-appointment-only space. It features dreamy vintage beach wear, plus memorabilia pegged to the area’s history — think surf boards and frayed shorts.
102 Industrial Road
- Rube (no website)
Curated apparel selection, including jeans and swimwear, plus leather goods and fragrances.
146 Main St.
- 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.
Looking for a group ride? Check with the following shops for information.
- Sag Harbor Cycle Company
- Rotations Cycling Center
- Montauk Bike Shop (guided trail rides)
Keep a musette bag rolled up in your jersey pocket.
You never know when the bounty of a roadside farmstand will prove too good to pass up.
Summer Cycling Events
Explore the “other fork” of Long Island. Ride on mostly flat and quiet back roads dotted with vineyards, horse farms and produce stands, and along the shore of Long Island Sound. Choose 25, 50, 72 or 100 mile routes.
Now in its 21st year, the Tour of the Hamptons begins in Southampton and wends east toward Montauk on a mostly flat course. Route options, which lead riders through historic hamlets, estate districts and farmland, include 25, 50, 70 and 100 miles, plus two 25-mile guided rides.