By: Lauren Matison
May 24, 2016

In this Strava era, where you can track the most popular bike routes in cities around the world, it’s never been easier for an out-of-towner to feel like a native. And while a classic local ride might be a great intro to a destination’s landscape and culture, the most memorable cycling experiences often come when we take the road less traveled.

Seeking a backyard tour of some of the coolest bike-crazy towns, we reached out to shops and pro cyclists for their uniquely designed two-wheeled adventures. From scenic climbs on the outskirts of Tokyo to the best brunch ride in Boulder, these 12 epic routes — plus 12 great bike-friendly hotels — will inspire you to pack up your bike and get lost this summer.

San Francisco

Where to ride: This 62-mile route may start predictably by crossing the Golden Gate Bridge, but pro cyclist and recent San Francisco transplant Ted King likes to mix up popular roads with some lesser known detours. Highlights along this Marin County loop — which goes out to Point Reyes Station — include a stop at Bovine Bakery and an unexpected turn with epic views. “A normal route would take you up Highway 1 all the way to Tam junction and back to Mill Valley. But those in the know will rip up Coastal Trail to Pantoll, which is all dirt and all badass,” says King.

Where to rest: Between its fleet of bright yellow complimentary cruisers and convenient location in Union Square, a breezy 30-minute ride to the Golden Gate Bridge, the newly opened Hotel Grace (summer rates from $178) is a restorative eco-friendly haven for cyclists. Reward a long ride with free pineapple cupcakes in the hotel lobby and a heavenly feast at nearby Hogwash or Mikkeller Bar.

Portland, Oregon

Where to ride: For local outdoor enthusiasts like Lindsey Morse of The Elegant Hippie, reinventing the adventure wheel every weekend is part of the thrill of living in Stumptown. Consider Morse’s 16-mile ride to “sample Portland’s funky charm” along the nature-filled Springwater Corridor Bike Trail. Take a quick detour around the Sellwood neighborhood then follow the trail along Johnson Creek to 82nd Street to load up on Koi Fusion tacos and Voodoo Donuts at Cartlandia, says Morese.

Where to rest: While bike-friendly hotels abound — there’s the Ace, Vintage Portland, Jupiter, Monaco — for a quintessential taste of Portlandia, Morse suggests heading to “an old farm-converted hotel with backyard distilleries and rock concerts on the lawn. Take the trail all the way to mile 15, then map the extra five miles to McMenamins Edgefield. Don’t forget the soaking pools!”

Tokyo, Japan

Where to ride: Spend an afternoon riding with master frame builder Keigo Hirota of Cherubim by Konno Cycle Works. Every Saturday, Hirota leads this 18-mile ride from the Cherubim factory out around the Machida and Tama areas of Tokyo. “Climbing the first hill, we look over the town and mountains, including Mt. Fuji, then go through downtown Tama, and finally climb the last hill to come back to the factory. I love this ride for the fellowship,” says Hirota. “The best method for us as bike builders is to communicate with the riders and share the joy, honor, and life itself.”

Where to rest: The sheer sensory overload of the world’s largest city makes Claska an ideal choice for a time out. Tucked away in the calm yet still kooky Meguro District, the hotel’s rooms (summer rates from $170), rooftop terrace, and custom-made fleet of Tokyo Bikes makes it easy to slip into a state of Zen.

Berlin, Germany

Where to ride: If you walk into bike boutique Prêt-à-Vélo and ask nice enough (and maybe buy something like a weinflaschenhalter), Lukas Grenzlehner might just share one of his favorite urban rides with you. From Prêt-à-Vélo in Berlin-Mitte, ride through Prenzlauer Berg, pausing at the Ernst Thälmann monument, before continuing on toward Friedrichshain. Admire the landmarked Oberbaum Bridge, then head to Treptower Park, where Grenzlehner can often be found eating traditional German donuts, known as quarkbällchen, from one of the waterfront stands. “Continue on to the center of Neukölln for dinner at Monella for amazing pizza and antipasti straight from South Tyrol,” says Grenzlehner.

Where to rest: With its on-site music studios, instrument room service, al fresco breakfast on the banks of the Spree River, and close proximity to the East Side Gallery monument to the Berlin Wall, you’d stay at this quirky Hotel Nhow Berlin (summer rates from $200), even if bikes weren’t available (which they are).

New York City

Where to ride: New York’s bike boom is showing no signs of fatigue, with over 1,000 miles of bike lanes and an increasing acceptance of two-wheeled commuters. Take a spin around Central Park and along the Hudson River Greenway, then escape the bustling Big Apple for this 44-mile ride, where you can catch Rapha’s Derrick Lewis enjoying verdant tranquility and some rewarding cold brews after three hours of pedaling up the city’s former water line. “The Old Croton Aqueduct is a bit of a secret gravel path that leads from the Bronx all the way to Croton Dam on a cross-bike-capable dirt trail,” says Lewis, who recommends rolling up to Peekskill Brewery for a recovery beer before catching the Metro North train back to NYC from nearby Peekskill Station.

Where to rest: When it comes to bikes, bites, and summertime bliss, The James is the best spot to bed down. Situated in Soho a few blocks from the Hudson River Greenway, the hotel (summer rates from $379) offers complimentary Public cruisers, breakfast at David Burke Kitchen, and a rooftop bar and pool with killer 360-degree views of the Manhattan skyline.

Boulder, Colorado

Where to ride: “This ride is my favorite way to beat the heat, enjoy the mountains, and have a culinary adventure in Boulder’s backyard,” says competitive cyclist Lentine Alexis, who’s also a Skratch Labs chef and Rapha Women’s Ambassador. The 54-mile loop ascends 6,234 feet throughout four hours and showcases the best of Colorado with fun dirt roads, switchback descents and stunning mountain vistas along the Peak to Peak Highway. “The climbs are completely epic and the scenery all along the route is beautiful. When you reach the top of the climb, the westerly views of the Rockies will take your breath away as you ride into Nederland, where refueling options abound,” says Alexis, who gets up early to hit Salto Coffee in time for a mid-ride brunch of homemade waffles with orange caramel.

Where to rest: Nestled in the heart of Boulder, yet within close range of some of the best biking and hiking trailheads, St. Julien caters to travelers who like vacations tailor-made for roughing it and relaxing. Various Build Your Own Adventure packages include two nights of luxurious accommodations, daily food and beverage credits, a $130 spa voucher per person, and a Hydropack backpack choc-full of Boulder-bred nibbles.

Venice, Italy

Where to ride: Lido and Pellestrina islands make for pretty leisure rides, but you’ll forget all about them after your next cone of gelato. For an unforgettable cycling experience, leave the crowded canals and drive an hour outside of Venice, where hors catégorie climbs and gorgeous views await. Whether you book an overnight adventure with the Italian Cycling Center or go it alone, make sure to do this 65-mile ride, which includes 7,300 feet of elevation gain, wild switchbacks, and a Giro d’Italia-approved summit finish atop Monte Grappa in the Venetian Prealps.

Where to rest: After braving the mountains and tourist mobs, retreat to JW Marriott Venice(from $300) on Isola delle Rose, a peaceful 40-acre island located just a 15-minute complimentary boat ride from St. Mark’s Square. This is the kind of place where allergies disappear and it feels like you’re oxygen doping (not surprising when you learn that the island operated a clinic to soothe respiratory ailments in the 1930s). In addition to taking deep revivifying breaths, get an outdoor massage at the Goco Spa, go for a dip in the rooftop pool, dine at Michelin-starred Dopolavoro, and pedal around olive trees, gardens, and a beautiful old church.

Burlington, Vermont

Where to ride: A visit to Burlington isn’t complete without cruising three miles out onto the Causeway and across Lake Champlain to explore the islands (with a little help from the bike ferry). But if you want to go off brochure, do local Lindsay Westley’s 50-mile Baby Gap loop. Beginning 20 minutes outside of Burlington, park at the Old Round Church and prepare for an exhilarating three-hour jaunt with 3,681 feet of climbing. “Start at Sweet Simone’s with a homemade bagel and a cup of locally roasted coffee,” says Westley. “Then climb south toward Hinesburg, where the roads out to Bristol are fast and mostly flat farmland, with plenty of great views toward the Adirondacks to the west.” Refuel at Bristol Bakery & Cafe with an egg taco — you’ll need the energy to get up over Baby Gap, which climbs 800 feet in less than four miles. If you’re feeling super motivated, stay on Route 17 to climb another 2.5 miles up over App Gap, which shoots upward for 1,200 feet of climbing on a sustained 8 percent grade. Otherwise, turn left on Gore Road, passing through Huntington and returning to the church on a mostly downhill road. “Finish the day with a Hatchet Burger and a pint of Hill Farmstead at the Hatchet Tap & Table,” says Westley.

Where to rest: If you had a Hotel Vermont in your hometown, it would be your go-to staycation. The hotel (summer rates from $239) regularly draws locals seeking inspired farm fresh fare at Hen of the Wood restaurant and weekly live concerts in the lobby. In addition to its fleet of complimentary Old Spokes Home bikes, it recently rolled out a bevvy of Budnitz Bicycles exclusively for guests.

Washington, D.C.

Where to ride: BicycleSPACE’s Francis Tatem says to pedal toward Anacostia, a quiet, overlooked cycling destination. The BicycleSPACE shop leads a weekly two-hour 25-mile Hills of Anacostia ride that Tatem says, “rewards you with some of the city’s best views.”

Where to rest: The sleek Mason & Rook Hotel (summer rates from $189) recently opened in the 14th Street neighborhood with complimentary Public bikes, sophisticated rooms with a James Bond vibe, a rooftop pool and lounge, and a cuisine-driven cocktail bar with over 200 rare spirits and whiskeys, eight draft beers, and four wine taps.

Melbourne, Australia

Where to ride: While everyone else is pedaling along Port Phillip Bay, revel in the beautiful backcountry en route to the summit of Mount Donna Buang. “The main road up is a scenic climb, but deviating from the well-worn track and going up the mountain via the back road lifts the riding experience to a whole new level,” says Ella CyclingTips co-editor Simone Giuliani. “The partly dirt back road is where you feel enveloped by the mountain ash and tree ferns of the Yarra Ranges National Park.” Throughout the 35-mile Mt Donna Buang loop, which starts at the Cog Bike Café in Warburton, you’ll ascend over 4,300 feet and enjoy spectacular views of Melbourne, Yarra Valley, and the Victorian Alps.

Where to rest: In the St. Kilda Road district, take out a Krona bike from The Blackman(summer rates from $299), an art and food lovers boutique property, and pedal along the bay on Beach Road to Aspendale for a postcard perfect picnic in front of the famous colorful huts.

Montreal, Canada

Where to ride: Locals love riding along the Lachine Canal and St. Lawrence River, with stops at Atwater Market, sculpture-dappled Park René Lévesque, and St. Ambroise Terrace for a micro brew. But as blissful as these car-free roads may be, they’re also sure to be crowded on a sunny summer day. Cycle Paul’s Jenny Ryan suggests a scenic 24-mile ride in the West Island of Montreal on Chemin Senneville. “This ride can start or end in St-Anne-De-Bellevue, with tons of wonderful coffee, ice cream, and restaurant spots,” says Ryan. “What makes this ride amazing is the peacefulness of the neighborhood. It’s truly a wonderful place to disconnect from life for a little while.”

Where to rest: Québec accommodations don’t get much more charming than Le Petit Hôtel(summer rates from $259), a modish property surrounded by 17th century buildings in the heart of Old Montreal. The hotel offers complimentary breakfast and city cruisers available 24/7.

London, England

Where to ride: Cycle Surgery’s Robin Holloway kicks off his favorite 50-mile ride in West London by pedaling through the suburbs and into Richmond upon Thames. Continue on toward Twickenham and Hampton Hill, stopping for a pastry at Cavan Bakery. “Straight as an arrow, head through all the major road junctions bypassing Walton and following the signs to Chertsey and Virginia Water lake, the gateway to Windsor Great Park, which is absolutely beautiful,” says Holloway.

Where to rest: A stay at Sanderson is like falling down the best kind of rabbit hole, and not just because there’s a Mad Hatter’s Afternoon Tea. Though the hotel is located in London’s West End, every inch of the landmark property, from the rooms (summer rates from $359) to the Courtyard Garden to the Purple Bar and Billiard Room, offer a wonderful whimsical smack in the face that’s hard to leave, even if complimentary bikes are waiting to whisk you away.