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Hiking Trip Odyssey 2018 New England Rambler new

Dates: 9/8 - 27, 2018

(20 days,19 nights;)



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


Segment 2: 9/19 - 27 (8 nights)


Assembly Point: Brattleboro, VT

(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.

Meeting time: airport 12 pm, hotel 4:00 pm

Drop off time: airport - 4 pm

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.

Double Booking: $8,295/person

Single Booking: $10,145

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

Roommate Rebate: $1750

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

Segment 2: 9 days DB:$3,995; SB:$4,975; RR:$930

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 built 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 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 1
   Arrive, assemble, bike fitting, orientation dinner  
Day 2 Brattleboro - West Dummerstund Covered Bridge - Townsend - Manchester, VT 47 miles
Day 3

Manchester - Fair Haven - Middlebury, VT

68 miles
Day 4 Middlebury - Port Henry - Bridge Across Lake Champlain - Keene - Lake Placid, NY

69 miles

Day 5

Lake Placid Layover Day - Home of the 1932 and 1980 Winter Olympics

Day 6 Lake Placid - Ausable River - Ausable Chasm, NY - Ferry Across Lake Champlain - Burlington, VT 41 miles
Day 7 Burlington - Ben & Jerry's Factory tour - Stowe, VT 39 miles
Day 8

Stowe - Smuggler's Notch - Belvidere - Newport, VT

63 miles
Day 9 Newport - Canaan - Dixville's Notch, NH 61 miles
Day 10 Dixville's Notch - Gorham - Pinkham Notch, NH 71 miles
Day 11 Pinkham Notch - Conway – Moultonborough – Wolfeboro, NH 56 miles
Day 12 Wolfeboro, NH layover day BEGIN SEGMENT 2
Day 13 Wolfeboro, NH - Limerick – Sebago Lake –763 Sebago Road, Sebago, ME 49 miles
Day 14 Sebago - Raymond – Freeport - L.L. Bean – Brunswick, ME 48 miles
Day 15 Brunswick - Bath - Boothbay Harbor – New Castle - Pemaquid Point, ME 67 miles
Day 16 Pemaquid Point – Friendship - Clark Island, ME 60 miles
Day 17 Clark Island - Marshall Point lighthouse – Rockland – Camden, ME 50 miles
Day 18 Camden - Belfast - Penobscot Narrows Bridge – Blue Hill, ME 68 miles
Day 19 Blue Hill – Ellsworth - Mt Desert Island – Cadillac Mt - Bar Harbor, ME 52 miles
Day 20 The Quiet side of Acadia: Bar Harbor - Bass Harbor – Oldhouse Cove, ME 33 miles

Total cycling mileage: 965

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Routes, mileage and accommodations are subject to change due to safety, road/trail conditions, weather and availability.