Odyssey 2018 New England Rambler

September 8 - 27, 2018

(20 days, 19 nights; Sat - Thu)

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Double Booking


Single Booking


Roommate Rebate


Includes all lodging, all breakfasts and dinners, van shuttles, van support, park entrance fees, leaders, tour maps and narratives.

Assembly Point

Brattleboro, VT

A driver’s shuttle will be available between Wolfeboro, NH and the start and end of the tour. Cars can be left in Wolfeboro for the duration of the tour.

Timberline van shuttle is included from Boston Logan International Airport to Brattleboro prior to the tour, and from Acadia National Park to Bangor International Airport following the tour.

Not included: Airline service; Guide Gratuity.

Segment 1: 9/8-18 (11 nights)

Segment 1: 11 days DB:$4,795; SB:$5,675; RR:$830

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Segment 2: 9/19 – 27 (8 nights)

9 days DB:$3,995; SB:$4,975; RR:$930

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Meeting Time

Boston Airport 12:00 pm, Boston Hotel 12:45 pm, Brattleboro Hotel 4:00 pm

Drop-off Time

4 pm

From the covered bridges of Vermont to the lobster laden waters of the Maine coast, this tour will ramble through some of the oldest established villages of the country for a gorgeous extended cycling trip. The new owner of Timberline Adventures grew up in northern New York, lived in Vermont and has cycled and hiked extensively in the New England states. This opens up new territory to our tours and we are happy to bring our new discoveries to you in our New England Rambler. Every day we’ll be treated to wonderful cycling, great food, unique experiences, and the warmth of New England hospitality.

We start in the southern hub of Vermont in Brattleboro, known for its fun, funky arts vibe. Our first day we cycle past two iconic covered bridges, with many more to come, as we wander through the Green Mountains and quintessential New England towns complete with white steepled churches and cozy country inns. We enter the Champlain Valley, stopping in Middlebury, home of one of the most respected small liberal arts colleges of the country – Middlebury College. We cross the southern terminus of Lake Champlain on a new bridge build with cyclists in mind, and enter the heart of the Adirondack Mountains. A layover day in Lake Placid gives plenty of time to explore the home of two Winter Olympics – 1932 and 1980. Continuing down the Ausable River will bring us to awesome Ausable Chasm and back to Lake Champlain. We’ll enjoy a ferry ride across the lake back to Vermont and Burlington, the “Queen City” of Vermont. From here we wander through the iconic Vermont ski areas of Stowe and Smuggler’s Notch, not forgetting to stop for a tour of the Ben and Jerry’s factory! Then it is up to the northern boundary of the country where French speaking Quebec leaves its influence in the small towns nearby.

Entering New Hampshire, we ride through several “Notch” towns and skirt the slopes of Mt. Washington, the highest peak in the Northeastern United States, before zooming down to the Lakes Region of New Hampshire and a ride along the edge of Lake Winnepesaukee. Here we spend a relaxing layover day in Wolfeboro, NH, the oldest summer resort in America, with a boat tour, hike, museum tours, or just a beach day and some local ice cream.

The second half of our tour begins in the lakes and ends at the ocean. We will cycle around Sebago Lake, the deepest and second largest lake in Maine, before curving down to the Maine coast. With more coastline than California, 3478 miles, touring the Maine Coast is a journey. We will cycle the best of the Maine Coast from the quiet elegance of Brunswick and up the coast to Bar Harbor. We will visit some of the most scenic of Maine’s 57 operating lighthouses, a fascinating link to region’s nautical history. The tour will reach out-of-the-way places like Clark Island, Pemaquid Point and Sprucehead. We may even meet the lobsterman who caught our lunch during our visit to Young’s Lobster pound in Belfast. Exploring famous coastal towns like Boothbay Harbor, Blue Hill, Camden and Bar Harbor is on the agenda. A victory lap through Acadia National Park will be a fitting finish for our grand New England Rambler Cycling Odyssey.



Day 1Arrive, assemble, bike fitting, orientation dinner
Day 2Brattleboro - West Dummerstund Covered Bridge - Townsend - Manchester, VT47
Day 3Manchester - Fair Haven - Middlebury, VT70
Day 4Middlebury - Port Henry - Bridge Across Lake Champlain - Keene - Lake Placid, NY80
Day 5Lake Placid Layover Day - Home of the 1932 and 1980 Winter Olympics
Day 6Lake Placid - Ausable River - Ausable Chasm, NY45
Day 7Ferry Across Lake Champlain - Burlington - Ben & Jerry's Factory tour - Stowe, VT35
Day 8Stowe - Smuggler's Notch - Belvidere - Newport, VT68
Day 9Newport - Canaan - Dixville's Notch, NH67
Day 10Dixville's Notch - Gorham - Pinkham Notch, NH58
Day 11Pinkham Notch - Conway – Moultonborough – Wolfeboro, NH68
Day 12Wolfeboro, NH layover day BEGIN SEGMENT 2
Day 13Wolfeboro, NH - Limerick – Sebago Lake –763 Sebago Road, Sebago, ME49
Day 14Sebago - Raymond – Freeport - L.L. Bean – Brunswick, ME48
Day 15Brunswick - Bath - Boothbay Harbor – New Castle - Pemaquid Point, ME67
Day 16Pemaquid Point – Friendship - Clark Island, ME60
Day 17Clark Island - Marshall Point lighthouse – Rockland – Camden, ME50
Day 18Camden - Belfast - Penobscot Narrows Bridge – Blue Hill, ME68
Day 19Blue Hill – Ellsworth - Mt Desert Island – Cadillac Mt - Bar Harbor, ME52
Day 20The Quiet side of Acadia: Bar Harbor - Bass Harbor – Oldhouse Cove, ME33

Total Distance: 965 miles

Inn Highlights

Odyssey 2018 New England Rambler

September 8 - 27, 2018

(20 days, 19 nights; Sat - Thu)