Boston to New York Cycling

Cycle from Boston to New York while raising money for charity


Take on this incredible 320-mile bike challenge from Boston, Massachusetts to New York City, taking in four iconic states on the east coast of the USA.

Our journey traverses the path that led to American independence. We start in New England’s capital and one of America’s oldest cities, Boston. With its grand architecture and world-renowned academic and cultural institutions, it is the perfect starting point. This unique cycling road trip then takes us on an exceptional journey through quaint communities, untouched coast, colonial villages, rolling hills, and seaside towns with deep breaths of invigorating salted air from the beautiful Atlantic coast.

Our final push to New York City takes us through some of the most well-known areas of the region including Queens, Brooklyn and Manhattan. Our finish line over the Brooklyn Bridge delivers us into the heart of America’s largest and most famous city, the Big Apple.



Upon arrival in Boston, Massachusetts, you will be met by our guides and transferred to our hotel in Seaport, a stone’s throw from the site of the Boston Tea Party of 1773, a key event in the American Revolution. We’ll have a briefing by our guides then have the afternoon to explore this historic city.

LODGING: Seaport Hotel

MEALS: On own



After breakfast and bike fittings, we’re fueled for our challenge. We make our way through city traffic to the quieter roads of our mostly flat route. Today gets us used to our saddles, riding through the familiar sounding towns of Weymouth, Kingston, and finally Plymouth, famous for Plymouth Rock, the site of the Mayflower landing in 1620.

LODGING: Best Western Cold Springs

MEALS: Breakfast, Lunch, Dinner

RIDING: 45 mi

ELEVATION: + 2018 ft


We have an early start to one of our longest and prettiest days. We follow the coast before going inland to quiet tree-lined roads leading into Providence, RI. We hit Scenic Route 1, taking in an amazing coastal ecosystem with countless song, shore and wading birds. We overnight in the small summer beach town of Gansett.

LODGING: Atlantic House Narragansett

MEALS: Breakfast, Lunch, Dinner

RIDING: 88 mi

ELEVATION: + 3837 ft


This morning takes us to a lighthouse and through a beautiful park before heading into Connecticut, our third of four states on this epic journey. We hit some challenging hills, today, and are rewarded with ice cream in the historic seaport town of Mystic, Connecticut. We continue onto New London, where we will overnight near the port.

LODGING: Clarion Inn New London

MEALS: Breakfast, Lunch, Dinner

RIDING: 58 mi

ELEVATION: + 3046 ft


We are back in the saddle for our longest day on this biking challenge! We first board a ferry for a 1.5 hour crossing to Long Island, New York. We ride 35 miles along a vineyard-dotted route to our first hill of the day at Port Jefferson, then spend the afternoon winding through quaint, wooded residential areas, until our final ride into Woodbury.

LODGING: Best Western Woodbury Inn

MEALS: Breakfast, Lunch, Dinner

RIDING: 90 mi

ELEVATION: + 3315 ft


Today marks the last day of our challenge. Local bike paths and routes lead us through the city to stunning views of Manhattan and the Statue of Liberty! We ride over the Brooklyn Bridge to our finish line where we celebrate with team photos and a special evening dinner to revel in our accomplishments.

LODGING: Best Western Seaport Inn

MEALS: Breakfast, Lunch, Dinner

RIDING: 40 mi

ELEVATION: + 1647 ft


After a well-earned night of rest, we have free time to enjoy this fantastic city. Whether you’re interested in shopping, museums, galleries or a walk around Central Park, New York will not disappoint. We transfer to JFK Airport for our flight home, taking with us memories that will last a lifetime.


MEALS: Breakfast


What’s Included?Riding the Brooklyn bridge

  • Airport transfers
  • Professional safety-certified guide(s) and bike mechanic(s)
  • 1 Challenge/Charity Representative TBD
  • 6 nights lodging (double occupancy)
  • Vehicle support throughout trip
  • Comfortable, well-tuned hybrid bikes (upgrades available)
  • All meals per itinerary + snacks, water, drinks
  • All permits and park fees
  • Local taxes, dining and housekeeping gratuities

Group Size

Min: 20 pax | Max: 60 pax

CONTACT US for a customized itinerary and costs.

Brooklyn Bridge and City2

New London Ferry Crossing