Boston to New York Bike Ride – Great Freedom Adventures
tour-item-template-default,single,single-tour-item,postid-3556,mkd-core-1.1.1,mkdf-social-login-1.1,mkdf-tours-1.3,voyage child theme-child-ver-1.0,voyage-ver-1.3,mkdf-smooth-scroll,mkdf-smooth-page-transitions,mkdf-ajax,mkdf-grid-1300,mkdf-blog-installed,mkdf-header-standard,mkdf-no-behavior,mkdf-default-mobile-header,mkdf-sticky-up-mobile-header,mkdf-dropdown-default,mkdf-light-header,mkdf-medium-title-text,wpb-js-composer js-comp-ver-6.6.0,vc_responsive

Boston to New York Bike Ride

Boston to New York Bike Ride

per person

5borobiketourBike Boston to New York

Four States and Five Boroughs 
Challenge yourself to bicycle 250 miles from Boston to New York City, connecting the east coast’s premier cities, each distinctly its own place and both supremely exciting. And if that isn’t enough of an adventure, top it off with the 40-mile Five Boro Bike Tour, America’s largest cycling event.

5 Boro Bike Tour

The 5 Boro Bike Tour is a rolling festival through all five New York boroughs on traffic-free streets. Pedal through Central Park in Manhattan, the vibrant streets of the Bronx, large and diverse Queens, the close-knit neighborhoods of Brooklyn and finally, surrounded by New York Harbor, the borough of Staten Island.

Four States, Five Boroughs and One Good Time
Four States and Five Boroughs is a ride to remember, encompassing iconic urban scenes, livable suburban towns, and peaceful rural landscapes, all highlighting the diverse land and the wonderful people that call this part of America home. Challenge yourself to ride Boston to New York with Great Freedom Adventures!

Tour Highlights:

  • Bike through four states in four days
  • Visit and stay overnight in the premier cities on the US east coast – Boston and New York
  • Participate in New York’s famed Five Boro Bike Tour, America’s largest cycling event
  • Stay in charming and vibrant coastal New England towns along the way
  • Pedal through diverse landscapes and seascapes of southern New England and New York
  • Visit Mystic Seaport, a living history museum depicting 19th century coastal New England life
  • Enjoy a scenic ferry ride
  • View the vineyards and farmland of eastern Long Island
  • Visit a winery and a brewery
  • Bike through Flushing Meadows Park, former site of two World’s Fairs
  • Visit the New York State Pavilion in the park, named a “National Treasure” in 2014, and see the iconic Unisphere
  • Cycle care-free and unencumbered with guides, van support, luggage transport and meals, snacks and cold drinks provided along the way

Tour Reviews & Testimonials


    Day 1 - Boston

    mystic-seaport-2Visit the sites of your choice in Boston then check in at the hotel in downtown Boston to meet your guides and fellow travelers. Guides will fit those who are renting bikes at this time. Then, enjoy a ride-fueling welcome dinner together.

    Day 2 - Boston to Rhode Island

    bike-new-york-2Take pre-ride photos on a stunning city plaza next to a fountain and a long reflecting pool with iconic Boston skyscrapers and historic buildings as the backdrop. Depart downtown Boston pedaling through an urban landscape of  bustling neighborhoods and city parks, predominately on bike lanes and paths. Boston’s suburban towns gradually give way to rural regions of horse farms and stately colonial homes. Continue south passing wildlife areas and reservoirs before entering Rhode Island. Arrive at the hotel, then enjoy dinner at an Italian restaurant. Biking Mileage: 50

    Day 3 - Rhode Island to Connecticut

    bikenewyork8rCycle through colonial Rhode Island towns and fertile farmland. Enter Connecticut and pedal along a ridgeline offering views of open fields and distant hills. Enjoy lunch at a turkey farm, and experience the freshest turkey sandwiches ever. Arrive at Mystic, a historic coastal town first settled in 1684. Explore Mystic Seaport, a living history museum with villages and ships depicting 19th century coastal New England life. Later, walk the charming town center with unique shops, pubs and cafes and watch the gears and counterweights in action as the Mystic River Bascule Drawbridge opens to let boats through. Enjoy dinner and lodging in Mystic. Biking Mileage: 62

    Day 4 - Connecticut to New York's Long Island

    mystic-rCross Long Island Sound by boat, arriving at the eastern tip of Long Island. Cycle along the shoreline, then through a landscape of lush vineyards and colorful farmstands. Enjoy lunch at a winery, then continue to Port Jefferson, a picturesque harborside village and historic shipbuilding center. Explore the charming streets and shops, then head to the brewery for some craft beer tasting before dinner. Stay at an inn in the heart of town and overlooking the bustling waterfront. Biking Mileage: 61

    Day 5 - Long Island to New York City

    mystic-seaport-3Continue cycling through western Long Island to the New York City borough of Queens. Pedal through Flushing Meadows Park, former site of two World’s Fairs, and view the iconic Unisphere. Cross over the bridge offering sensational views of the city skyline to reach the island of Manhattan, then cycle the bike path along the East River to the New York Bike Expo. Enjoy the exposition and receive your packet for the Five Boro Bike Tour. Spend the night in Manhattan, enjoying city life in “the city that never sleeps.” Biking Mileage: 72

    Day 6 - Bike New York's Five Boro Bike Tour

    5borobiketourr1Today, ride together in the nation’s largest cycling event – the Five Boro Bike Tour.  Join 32,000 fellow cyclists to bike New York’s five boroughs on traffic-free streets. Bike through Central Park and cross over five bridges including the spectacular Verrazano-Narrows Bridge. Enjoy the post-ride festival to conclude your epic ride through four states and five boroughs.   Biking Mileage: 40   Please Contact Us for detailed itinerary and arrival and departure information.

    colonnade-hotelThe Colonnade Hotel, Back Bay, Boston, MA - 1 NightThis luxury Boston hotel is centrally located for easy access to numerous Boston attractions. It is adjacent to Boston’s main shopping district and the Back Bay, a charming residential neighborhood. Amenities include an on-site restaurant and bar, fitness center and a rooftop pool with sweeping views of the Boston skyline and the Prudential Center.

    hampton-innHampton Inn & Suites, Smithfield, RI - 1 NightEnjoy Rhode Island hospitality in this newer hotel. Amenities include an indoor pool and fitness center.
    inn-at-mysticInn at Mystic, Mystic, CT - 1 NightThis country inn, located in historic Mystic, CT, offers wonderful views of Mystic Harbor and Fishers Island Sound. Amenities include an on-site restaurant and bar, pool, walking trails and a tennis court. Walk to restaurants and shops in lovely Mystic.
    danfords-hotelDanfords Hotel & Marina, Port Jefferson, NY - 1 NightThis fine hotel is located directly on Long Island Sound, in the heart of Port Jefferson, a historic shipbuilding village. Walk to numerous shops and restaurants and to the brewery. Hotel amenities include an on-site restaurant and bar, spa, salon and a fitness center.
    gild-hallGild Hall, New York, NYGild Hall, a Thompson Hotel, is a unique Manhattan Hotel featuring a warm, masculine décor, spacious rooms and impeccable service. It features an excellent gastro-pub restaurant on site. The hotel is convenient to the start and finish of the Five Boro Bike Tour.

    2022 Dates

    April 26-May 1

    2022 Prices (Good till 11/15/21)

    $3,095, per person based on double occupancy. Single Supplement: $895.

    Trip Length

    6 days, 5 nights


    Boston, MA/New York, NY

    Daily Mileage


    Cycling Level



    Paved roads with some bike paths. Flat to rolling hills.

    Bikes: You may bring your own bike or use one of ours. GFA bikes are high quality, lightweight, available with either drop or straight handlebars and are equipped with computer, mirror, waterbottle, handlebar bag, map case and seat pack with essentials. What's Included:
    • Five days of bicycling (four without 5 Boro Bike Tour)
    • Bicycle and helmet rental
    • Five nights lodging
    • Five breakfasts
    • Three dinners
    • Four lunches
    • Ferry ticket for passenger and bike
    • Entrance to Mystic Seaport
    • Beer tasting
    • Guides
    • Van support
    • Luggage transport
    • Daily snacks and cold drinks
    • Maps and cue sheets
    • Tax and gratuities for meals and side excursions
    • Water bottle
    Frequent Adventurers, GFA alumni, may deduct 5% from the tour price. Please contact us for youth and group rates. Custom dates and duration are available for groups of six or more. Please Contact Us for detailed itinerary and arrival and departure information.

    Be The First To Know About New Tours

    Be the first to get latest updates and information about new tours straight to your email inbox.