Odyssey 2021 – East Coast Greenway-I

September 8 - 24, 2021

(17 days, 16 nights; Wed - Fri)

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Bonus Tour

Double Booking


Single Booking


Roommate Rebate


Includes all lodging, breakfasts, snacks and dinners, support van, leaders, tour maps, cue sheets, gpx files & narratives.

Assembly Point

Calais, Maine

Timberline van shuttle is included from Bangor, ME to Calais

Not Included: Airfare to Bangor International Airport; Alcoholic Drinks; Guide Gratuity

Note: The number of single bookings are limited

Meeting Time

1pm in Bangor, 4pm in Calais

Drop-off Time

9 am New York City departure

The East Cost Greenway

Fifteen states,  450 cities and towns and 3,000 miles from Maine to Florida on a safe biking route through the country’s most populated corridor.  That is the East Coast Greenway. Our Odyssey Journey will take us on the first fully-supported, end-to-end tour on the Greenway.  We are running this tour in partnership with the East Coast Greenway Alliance, the folks who have worked tirelessly to put together the route, and continue to work to add Greenways and improve the entire journey.  For every guest on our tour, we will make a donation to the Alliance. Dinner is at local restaurants and nights are spent in local hotels.  The trail is a combination of paved bike paths, back roads and unpaved path sections.  Hybrid or gravel bikes are perfect for this epic ride.  Traditional road bikes with some wider tires can also work.  No matter your steed, there is a fabulous adventure ahead.

From Backwoods to City:

The first segment of this epic ride along the East Coast Greenway begins at the Maine – Canada border on the banks of the St. Croix River. The first two days are mostly on the unpaved Down East Sunrise Trail which takes us for 87 miles through the woods of Maine.  There is an alternate paved route on this section.  Then we continue beside the sparsely populated waterways of the coast, working our way down to Portland. We stay on the coastal road for the entire length of New Hampshire’s Atlantic shoreline and enter Massachusetts for our first layover day in Marblehead.  Stroll the old neighborhoods, watch the yachts and feast on seafood – you’ve earned it.  From there we continue south by hugging the coast right into Boston. Then we loop through middle Massachusetts, and swing around to cut through Rhode Island and across to Connecticut.  From there the route follows the Long Island Sound into the Bronx and down the Hudson River right into the heart of Manhattan for our overnight and layover day.

Link to our East Coast Greenway Tour Overview

Link to the entire Greenway Map


Day 1Arrive, assembly, bike fitting, Orientation Dinner Calais, ME
Day 2Calais-Moosehorn National Wildlife Refuge -Down East Sunrise Trail - Machias, ME46
Day 3Machias - Down East Sunrise Trail - Ellsworth, ME57
Day 4Ellsworth - around West Penobscot Bay - Camden, ME64
Day 5Camden - Owl's Head - Waldoboro - Newcastle, ME58
Day 6Newcastle - Brunswick - Freeport - Portland, ME69
Day 7Portland - Eastern Trail - Kennebunk - Portsmouth, NH57
Day 8Portsmouth - Newburyport - Topsfield Linear Common - Marblehead74
Day 9Layover Marblehead, MA
Day 10Marblehead - Boston - Charles River Esplanade - Hudson, MA55
Day 11Hudson - Worcester - Blackstone Greenway - Pawtucket, RI64
Day 12Pawtucket - Providence - Washington Secondary Trail - Putnam, CT55
Day 13Putnam - Airline North State Park Trail - Hop River State Park Trail - Hartford , CT64
Day 14Hartford -Farmington Canal Heritage Trail - Southington - New Haven, CT58
Day 15New Haven - Bridgeport - Fairfield - Stamford - Port Chester, NY68
Day 16 Port Chester - New Rochelle - Pelham Bay Bridge - NYC Greenways - Broadway Bridge - Hudson River Greenway - Manhattan, NY36
Day 17New York City - transition day

Total Distance: 825 miles

Odyssey 2021 – East Coast Greenway-I

September 8 - 24, 2021

(17 days, 16 nights; Wed - Fri)