Leaves to Liberty
September 16 - October 3, 2027
Difficulty: Good Pace +
Average Distance Per Day: ≈ 60 miles
Average Climbing Per Day: ≈ 3550 feet
Beginning in Portland, ME, the route winds west toward Mt. Washington and the White Mountains before descending into the peaceful beauty of Lake Champlain. From Burlington, riders continue southeast through Connecticut, Rhode Island, and New York, finishing with a volunteer build day in New Rochelle and a celebratory visit to New York City—including an optional ferry to take in the sight of Lady Liberty.
For cyclists seeking purpose, beauty, and camaraderie, this ride offers all three in abundance.
What to expect on the Leaves to Liberty Event:
- 12 days of riding, averaging about 60 miles per day
- Two volunteer days in communities along the way
- Cool crisp mornings & moderate high temps
- A barrage of fall colors around every turn
- Combination of roads, crushed limestone rail trails, city, and rural riding. Mixture of paved and unpaved surfaces.
Registration opens at 10am on September 1, 2026. Until then…
A Fantastic Fall Ride
The 2027 Leaves to Liberty event is more than a cycling event—it’s a two‑week immersion into the colors, communities, and character of New England.
Riding 750 miles and seven states, riders will experience a mix of both New England towns and streets, but also quiet rail
trails, winding rural roads, limestone paths, and two meaningful volunteer days that connect the journey to the mission.
While the cycling attracts many people to our events, most participants quickly learn they’re part of something far grander than just a ride. Join us to learn why.
There is a lot to love on the Bike Adventure’s Leaves to Liberty bicycle event!
Schedule: Leaves to Liberty (Sep 16 - Oct 3, 2027)
| Day | Date | Depart | Arrive | Mileage | Climbing |
| Thursday | Sep 16 | Portland, ME | Arrive | — | |
| Friday | Sep 17 | Portland, ME | Windham, ME | 22 | 1200 |
| Saturday | Sep 18 | Windham, ME | Windham, ME | VOLUNTEER | — |
| Sunday | Sep 19 | Windham, ME | Fryburg, ME | 47 | 2400 |
| Monday | Sep 20 | Fryburg, ME | Whitefield, NH | 70 | 4000 |
| Tuesday | Sep 21 | Whitefield, NH | Morrisville, VT | 71 | 4100 |
| Wednesday | Sep 22 | Morrisville, VT | Burlington, VT | 64 | 5000 |
| Thursday | Sep 23 | Burlington, VT | Montperlier, VT | 45 | 2500 |
| Friday | Sep 24 | Montperlier, VT | Lebanon, NH | 67 | 3700 |
| Saturday | Sep 25 | Lebanon, NH | Concord, NH | 61 | 3000 |
| Sunday | Sep 26 | Concord, NH | Concord, NH | OFF | — |
| Monday | Sep 27 | Concord, NH | Marlborough, MA | 77 | 3700 |
| Tuesday | Sep 28 | Marlborough, MA | Norwich, CT | 83 | 4700 |
| Wednesday | Sep 29 | Norwich, CT | Bridgeport, CT | 82 | 4000 |
| Thursday | Sep 30 | Bridgeport, CT | New Rochelle, NY | 50 | 2600 |
| Friday | Oct 1 | New Rochelle, NY | New Rochelle, NY | VOLUNTEER | — |
| Saturday | Oct 2 | New Rochelle, NY | New Rochelle, NY | OFF | — |
| Sunday | Oct 3 | New Rochelle, NY | Depart | — | |
| Total: | 739 | 40,900 | |||
| Average: | 62 | 3408 |
Transportation
We pick-up and drop-off from local transportation hubs.
Arrival Airport: (PWM) Portland. Arrival Train/Bus Station: (POR)
If you prefer to fly into Boston, MA (BOS), consider the Concord Coach Lines bus from the Boston Airport to the Portland POR station. Transportation not be provided by the Fuller Center from Boston, MA.
Arrive before 3pm on Sept 16, 2027
Departure Airport: (HPN) New York Westchester
If you fly out of one of the other airports in NYC or arrange a flight on October 2, 2027 you will need to arrange a shuttle to the airport.
If you fly out of Westchester, NY, plan your departure after 6 AM on October 3, 2027.
For more discussion and advice around arrivals and departures, please see our transportation page. Note that the trip leader will be in touch via email in the months ahead of your trip with more specific details.
What's Included
- Breakfast, lunch items, and 5-6 dinners per week
- Rest stops approximately every 20-25 miles
- Overnight host facilities
- Shower arrangements
- Bike Adventure jersey, t-shirt and water bottle
- Routes and route sheets
- Support Vehicle(s)
- Airport pick-up and drop-off (within specified limits)
- Laundry
- Volunteer build day(s)
- Fundraising tools
- Ride leadership and organization
- Supportive, faith-based community environment
- Purpose and mission for your ride
Our amazing hosts, volunteers and riders often go far above and beyond this list. We invite you to come ready to be amazed by the generosity of others — and open to the nudges of the Spirit on how you, too, can be a blessing.
“This sounds great, can we talk before I join?”
“Tell me more about what to expect on this adventure”
