Created in the seventeenth century [circ 1673] by the postal service to connect Boston and New York it would be another 100 years before the first stagecoach travelled this important route and a few years later [1789] saw George Washington, the newly inaugurated first president of the United States of America,  travel this same route from New York on a visit to Boston City. Now you can cycle the same route on our fully supported cycle Boston To New York bike.

We don’t think you will find a more historic and beautiful route in the USA than this!

The Boston To New York Bike Ride

Total Distance: 454km
Total Ascent: 3,828m
Max Alt: 359m
Difficulty Grade: 3.5/5
7 Nights
Available for private groups
Thrill Score #10+
Guide Price: POA

On this historic and beautiful five day cycling route from New England’s capital, Boston, you can expect to cycle past historic landmarks, through colonial villages, seaside towns, and quaint communities on your way to the Americas most famous and historic metropolis, New York City. Once entering ‘the big apple’ you will ride your bike right down Manhattan’s east side taking in all the sights before crossing the iconic Brooklyn Bridge and returning and finishing in New York’s world famous Central Park!


Day One – Arrive Boston Logan airport – transfer to hotel. Times of recommended flights given at time of application. Build bikes before evening meal and early night.

Day Two – Boston to Worcester – 88km (55mi) +770m

Day Three – Worcester to Springfield – 90km (56mi) +1,056m

Day Four – Springfield to New Haven – 112km  (70mi) +593m

Day Five – New Haven to Greenwich – 88km  (55mi) +577m

Day Six – Greenwich to New York – 78km  (49mi) +417m

Day Seven – Free day in NYC!

Day Eight – Pack down and box bikes before return flight home.


Experienced Cycle Leader(s), Full Vehicle Support, Bike Mechanic, First Aiders, Baggage Transfer, 3/4 star Hotel Accommodation (7 nights inc Breakfast)

Not Included

Flights, Lunches, Evening Meals, Airport Transfers (optional)


Recommended flight information will be given on your application.To help us help you, It is important you notify us of any extraordinary travel arrangements you may have that prevents you from arriving at the recommended times.
Your personal bags will be carried by the support vehicle throughout the event.
We strongly ask your bikes to be transported by bike bags (semi-rigid/soft). Please do not arrive to the event with rigid bike travel boxes. Support vehicles will have limited space and unable stow large solid bike boxes as well as all luggage and equipment through the event.
Please contact us with any questions regarding flight transport of your bike, we will be more than happy to discuss this further with you.

Weather & Kit

Typically this event is run in late Spring or Early Autumn, we can expect warm, sunny weather, however we should also expect some cool mornings and possible precipitation, remember to bring layers – not heavy coverings.
This is a road bike tour. Your bike should be well maintained and in good running order with suitable ‘road gears’ and brakes.
A full kit list will be issued in your ‘Joining Instructions’ document after your application. We will be glad to discuss any aspect of kit and your bike with you, please call us anytime with any questions.

Fitness & Training

This is a level 3.5 cycle event. You will be capable of riding comfortably upto 120km in a day and/or used to riding distances upto 90km over hilly terrain – minimum. If you have any doubt as to your fitness regarding participation in this event please give us a cal and we will be more than happy to chat with you.

Click here for Training plan

Boston To New York Bike Ride Route

Boston To New York Route Profile

profile Boston to New York bike ride

To join us on our next epic ride to New York city register your interest today…

cycle Boston To New YorkTo participate on this incredible cycling holiday or for further information hit contact us  now…

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