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An Exclusive challenge offered only by Cycle of Life Adventures!

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In 2020, we reintroduced our Epic Appalachian cycling tour. We have brought back our former version of a ride, which parallels the Appalachian Trail, and combined it with our Blue Ridge Parkway and Skyline Drive tour. The tour starts in a rustic and rural western corner of Maine and parallels the Appalachian Trail on low volume surface streets to our termination point in Cherokee, NC.

This is an original route designed by Cycle of Life Adventures. This is a 28-day cycling experience that can be done entirely or in halves. The full experience congratulates you with 1,440 miles of riding and 107,000 feet of elevation gain.

The northern segment will include the wilderness of central Maine, the Green and White Mountains of New Hampshire and Vermont, the Berkshires of Massachusetts, the Red Mountains of Connecticut, Mountains of eastern and central PA and New Jersey, The Delaware Gap, The Pocono Mountains, and Gettysburg, PA.

After our mid-way break near Gettysburg, PA, we then have the hills to contend with. Big hills! They are beautiful, lush green and at altitude, so the temperatures will be nice for riding. Many miles of the southern segment will include the full length (105 miles) of Skyline Drive National Park and 469 miles of the Blue Ridge National Parkway.

Right out of the starting gate, you get to experience our favorite ride of this trip, the Kancamagus Highway. Then, we ride on the quiet roads and enjoy the rustic scenery of Vermont. Vermont bicycle touring is the granddaddy of bicycle travel and is still a popular destination today. Vermont and New Hampshire roads will be quiet because we are ahead of the “Leaf Peeper” season.

We visit the Robert Frost Museum and Norman Rockwell Museum. New England will be quiet at this time of their early tourist season and the rolling countryside orchards of western Pennsylvania and Maryland will be greening up. In most minds, one thinks of New York, Connecticut and Massachusetts as being nothing but city. Just 50 miles north of NYC, we find some charming small towns with rolling hills, rivers and great scenery, as well as one of the Vanderbilt mansions. You will have the thrill of riding your bike across the Hudson River on the walkway bridge. Don’t blink your eyes or you will miss our tiny crossing through the state of New Jersey.

Through most of Pennsylvania, we hug the valleys between Appalachian ranges, the Poconos and some parts of the Delaware Water Gap. The beautiful capital city of Harrisburg lends to some comfortable scenic bike trails along the Susquehanna River. With a break day coming up, we have few days to take us into some of our country’s most well-preserved and educational Civil War Battlefields and the historic town of Gettysburg. There are several types of tours for the battlefields of Gettysburg National Military Park to fill your rest day. We will also be adding or subtracting guests, as this is our halfway spot and a chance for others to join us on the southern half of the trip.

From Gettysburg, we will now head to Harper’s Ferry, WV, before we take on Skyline Drive and Blue Ridge Parkway. The southern portion of this epic journey takes us into a couple of wonderful National Park Inns like The Peaks of Otter, and Big Meadows in VA and Pisgah Inn in NC. These NP lodges have beautiful long-range views. There are many pull-offs, nearly 300 hundred overlooks, on Skyline and the Parkway. The road surfaces are nicely paved, but you will need bright head lamp and flashing tail lamps to find your way through the 27 tunnels that have been carved into the mountainsides along these roadways. Throw in some water shoes – we ride past cool mountain streams, waterfalls and swimming holes.

Small mountain towns of Meadows of Dan, Fancy Gap, Blowing Rock and Linville to name a few, will be our resting spots nightly before we wrap up our tour near the vibrant small city of Asheville, North Carolina. Think about meeting family and friends after the tour and stay a few extra days to enjoy local beer scene, the River Arts District and The Biltmore Estate.

Visit these sites for more information about the local areas: Bethel Maine  •  Norman Rockwell • Manchester VT •  Jim Thorpe PA • Gettysburg   • Harper’s Ferry WV •  Skyline Drive •  Blue Ridge Pkwy


If flying in, make your reservations to Portland, Maine International Airport for July 20, 2025.

  • Pick up will be at baggage claim by noon.
  • When flying out, drop off will be by noon on August 18, 2025 at Asheville, NC. Do not make reservations before 7pm if leaving on the 17th.
  • If you are driving to our starting hotel location, please arrive by 2pm in time for our bike fitting, social hour and orientation dinner.


All lodging is included

Special Note

This tour has different starting and finishing cities. Please book flights into Portland, Maine, and returning flights from Asheville, North Carolina.

We cannot accommodate tricycles or recumbent bicycles on our Epic tours.

Portland, ME airport pickup at noon. Orientation dinner at Bethel Inn Resort in Bethel, ME at 5:00pm.


Day 1

Bethel, ME – Conway, NH (50 miles; 1968′ elevation gain)

Highlights: Today’s ride takes us out of Bethel with nice rural routes along the Androscoggin and Saco Rivers. There is one climb of the day before we ride across the Maine/New Hampshire border a few times. Enjoy the White Mountain National Forest scenery near Gorham, NH. Tonight’s accommodations are right in Conway with walking distance to several restaurants and a 5-minute drive from outlet shopping.

Accommodations: Starting hotel is the Bethel Resort Inn, Bethel, Maine. Scenic Inn, Conway NH (casual)

Day 2

Conway – Woodville, NH (60.1 miles; 4027′ elevation gain)

Highlights: Our ride today is challenging. The first 18 miles are a steady uphill climb of 1 -3%, then a 5-mile finale’ to the top of Kancamagus Highway. All downhill following the rocky riverbed to a riverside picnic lunch near Loon Resort. Weather permitting, views of Mt. Washington, Mt La Fayette.

Accommodations: Nootka Lodge (casual)

Day 3

Woodville, NH – Woodstock, VT (57.3 miles; 2858′ elevation gain)

Highlights: Today we hug the Vermont/New Hampshire state line along the very scenic Connecticut River. Great lunch stop on the Green in Hanover, home to Dartmouth University. We cross the river into Vermont now and follow the White River before sneaking in the back way to Woodstock, Vermont. Quechee Gorge and Simon Pierce Glass blowing are wonderful stops. Today’s ride is rolling hills and a few small climbs.

Accommodations: Shire Inn (casual, Riverside, intown)

Day 4

Woodstock, VT – Manchester, VT (55.7 miles; 3996′ elevation gain)

Highlights: Before leaving town, try to visit the Billings Farm Museum and walk the downtown streets. Today’s ride is another challenging day with 2 big hill climbs near Okemo and Bromley Ski Resorts but, nice downhill riding, as well. Our home for the night is in Manchester Center with upscale outlet stores, the Orvis flagship store, fly fishing clinics, and fine dining possibilities.

Accommodations: Palmer House Resort (casual)

Day 5

Manchester Center, VT – Pittsfield, MA (68 miles; 3215′ elevation gain)

Highlights: Riding today with lots of rolling hills in both VT and MA. We travel along the Housatonic River and through the small western Massachusetts towns of Adams and North Adams. We are crossing the Appalachian Trail several times today and following the Ashuwillticook Rail Trail before coming into Pittsfield for our rest day.

Accommodations: Holiday Inn and Suites Downtown (business class)

Day 6

Highlights: Activities could include: a tour of Oliver Wendell Holmes home, Hancock Shaker Village, Norman Rockwell Museum, or local hikes and mountain bike tours in the Berkshires.

Day 7

Pittsfield, MA – Sharon, CT (59.4miles; 2728′ elevation gain)

Highlights: The long scenic riverside ride along the Housatonic River and the lowest points on the Appalachian Trail are just steps away from our route at various points today. The ride is relatively easy as we follow the valley through the beautiful MA and CT towns of Lenox, Stockbridge, Great Barrington, North Canaan and a lunch break at the charming Historical Society Park in Sheffield.

Accommodations: Sharon Country Inn (casual)

Day 8

Sharon, CT – Poughkeepsie, NY (53 miles; 2446′ elevation gain)

Highlights: We pick up our sixth state in just eight days. Early today, we cross into New York. We ride some nicely paved roads near Clinton Corners. There are long stretches of beautiful farms Our lunch stop today is the FDR Historic home site. Nearby is The Vanderbilt Mansion and the Culinary Institute of America, Rhinebeck, Hyde Park, Hudson River bridge and Hudson Valley Rail Trail

Accommodations: Hampton Inn – New Paltz

Day 9

New Paltz, NY – Milford, PA (64.5 miles; 2936′ elevation gain)

Highlights: We will rack up two more states today: New Jersey and Pennsylvania. Today’s ride takes us along the Neversink, Wallkill and Shawangunk Kill Rivers. We have several portions on the NY rail trail systems in Walden and Goshen, NY. There are fine examples of older rail bridges along the route. The route is rolling and follows the valley again today with one climb over the Appalachian ridge and into the small town of Milford, PA.

Accommodations: Tom Quick Inn (casual)

Day 10

Milford, PA – Jim Thorpe, PA (74 miles; 3631′ elevation gain)

Highlights: Today, we will parallel the Appalachian Trail for most of the route. If you look over your left shoulder, the AT will follow the ridge on the opposite side of the Delaware River. We have a beautiful ride all morning along the Delaware River with a lunch stop at the Little Gap covered bridge. As we pull away from the river, the afternoon takes us through fertile farmlands and the lush green Pocono Mountains. Our stop for the evening is the town of Jim Thorpe, named for the Olympic athlete. The town once known as Maulk Chunk was the site of coal mining along the Appalachians and brought out by steam engines along the Lehigh River.

Accommodations: The Inn at Jim Thorpe (historic)

Day 11

Jim Thorpe, PA – Grantville, PA (74.5 miles; 4126′ elevation gain)

Highlights: Today is just more beautiful rolling farmlands and barns in the Pennsylvania Dutch Country. We parallel the mountain range and skirt in and out of once thriving mining town of Schuykill Haven. Much of the local industry now lends itself to farming and small service towns as well as popular tourist attractions as Hershey Park. We follow part of the Swatara Rail Trail to our stopping point of Grantville.

Accommodations: Hampton Inn (casual)

Day 12

Grantville, PA – Gettysburg, PA (60.5 miles; 2615′ elevation gain)

Highlights: The Capital City Bike Trail follows the beautiful waterfront of the Susquehanna River. There you will see an abundance of retired and operational train bridges, tunnels and newly renovated recreational paths. Riding for the day is a small gradual uphill from the river valley, then rural farmland and small PA farming towns to our destination of historic Gettysburg. We will stay downtown and take in some of the battlefield, today and tomorrow, before we leave for Harper’s Ferry, WV.

Accommodations: Inn at Cemetery Hill (casual)

Day 13

Enjoy the day in the battlefields by vehicle, walking, or bike.

Total Miles – 677
Total Elevation Gain – 34,566 ft

Day 14

Gettysburg, PA – Harpers Ferry, WV (61 miles; 2452′ elevation gain)

Highlights: Today we gain two more states, MD and WV. We travel more back roads through farmland and around the battlefields of Boonsboro and Gettysburg. We do travel through the city of Frederick, MD, but try to stay on more residential and farming roads which parallel the new interstate and highway systems. We use part of the C&O Towpath to make our way into downtown Harper’s Ferry.

Accommodations: Quality Inn located in Historic District (casual)

Day 15

Harper’s Ferry, WV – Front Royal, VA (51.5 miles; 2900′ elevation gain)

Highlights: Scenic riding in the valley along the river in Shenandoah National Park

Accommodations: Hampton Inn (casual)

Day 16

Front Royal, VA – Big Meadows, Skyline Dr (56.5 miles; 7480′ elevation gain)

Highlights: This is the first of the “Big” riding days. Here, we start the Skyline National Parkway with spectacular scenery at numerous overlooks and a wonderful dinner at the National Park Lodge.

Accommodations: Big Sky Meadows Lodge National Park (casual)

Day 17

Big Meadows , VA – Waynesboro, VA (64.5 miles; 4573′ elevation gain)

Highlights: This is day two of Skyline Drive. We have numerous crossings of the Appalachian Trail. Quiet and low volume traffic on very nicely paved roads. There is no commercial traffic and no billboards on Skyline Dr. We take Skyline to its terminus where the next morning we start our venture southbound on the Blue Ridge Parkway.

Accommodations: Best Western Plus (casual)

Day 18

Blue Ridge Parkway entrance – Buena Vista/Lexington (58.5 miles; 5796′ elevation gain)

Highlights: The Blue Ridge Parkway was a Civilian Conservation Corp project started on September 11, 1935 for the purpose of connecting Shenandoah National Park to The Great Smoky Mountains National Park. There are 27 tunnels on the Blue Ridge Pkwy: one in Virginia and the remaining 26 in North Carolina. Today you will take on the first 45 miles of the 469 miles of this beautiful scenic roadway – “America’s Favorite Drive”.

Accommodations: Hampton Inn Historic District

Day 19

Highlights: The historic town of Lexington, VA. Horse capital of VA, Natural Bridge Park, Washington and Lee University, Virginia Military Institute. Do get lots of rest. The next two days are strenuous.

Day 20

Buena Vista , VA – US 460 Peaks of Otter National Park Lodge (57.5 miles; 6557′ elevation gain)

Highlights: Falling Waters Cascade, 15 overlooks, spectacular lodge setting at The Peaks of Otter National Parks Lodge. On today’s route, you will be at the lowest and highest elevations of the Virginia portion of the Blue Ridge Parkway, that means some hill climbing.

Accommodations: Peaks of Otter Lodge National Park Service (casual)

Day 21

Peaks of Otter, VA – Floyd, VA (79.5 miles; 6823′ elevation gain)

Highlights: Big climbs out of the Roanoke area of the Blue Ridge Pkwy. Due to heavy rains in Spring of 2020, we will have a detour from mile post 112 to 136 to reroute us around a road-wash and land slide. Specific stopping points are Mabry Mill and Rocky Knob Visitors Center and overlook.

Accommodations: Pine Tavern Lodge (casual)

Day 22

Floyd, VA – Glendale Springs, NC (102 miles; 9226′ elevation gain)

Highlights: Great quiet riding of the VA section of the Blue Ridge Parkway – 18 overlooks. Some of the quietest and most rural parts of the Blue Ridge Parkway. Cross into NC. If you ever get the opportunity, come back one summer evening to enjoy an outdoor music presentation at the Blue Ridge Music Center located at the state line.

Accommodations: New River Inns and Cabins

Day 23

Glendale Springs, NC – Linville Falls, NC (60.7 miles; 6376′ elevation gain)

Highlights: Great riding on the Blue Ridge Pkwy. Linville Falls, the most viewed water falls along the parkway. Moses Cone Manor Museum, Arts and Craft center housed inside of the manor home to Moses Cone, the Levi Straus of the East Coast. Famous Linn Cove Viaduct was the last 7.5 mile section on the Parkway completed in 1987. This is 52 years after the start of the BRP. Grandfather Mountain is private property and the owner would not give the National Park Service permission to dig on his mountain. Thus, the suspended Linn Viaduct.

Accommodations: Linville Falls Lodge (rustic)

Day 24

Linville Falls, NC – Asheville, NC (67.7 miles; 7709′ elevation gain)

Highlights: Blue Ridge cycling, Little Switzerland, multiple tunnels, Crab Tree Falls, and Mt. Mitchell, if you choose. Enjoy a nice evening out in downtown Asheville, my favorite small city in America. This vibrant downtown is packed with art, culture and dining opportunities ranging from upscale tapas bars to gourmet tacos. America’s largest private home, Biltmore, is located in Asheville.

Accommodations: Sheraton Downtown (business casual)

Day 25

Asheville, NC – Pisgah National Forest, Pisgah Inn (50.4 miles; 6943′ elevation gain)

Highlights: Blue Ridge Parkway riding, 11 tunnels, beautiful spot atop Pisgah Mountain for a wonderful dinner together at the lodge.

Accommodations: Pisgah Lodge (National Park Lodge)

Day 26

Pisgah Inn to Cherokee, NC, to the terminus of the Blue Ridge Pkwy (51 miles, 5518 ft)

Highlights: Shuttle back to Asheville Sheraton for our last night together. Choose to stay longer or catch a flight out of Asheville in the morning. Pat yourself on the back! You have just completed 761 miles and 72,333 ft of elevation gain on this southern segment.

Total Miles – 1,438
Total Elevation Gain – 106,899 ft
Average daily riding mileage – 60
Average elevation gain – 4,454 ft


  • All Lodging
  • Transfers to and from the airport
  • All breakfasts, picnic lunches and most dinners on riding days
  • Cocktail social hours on the 1st evening of each tour
  • Van support
  • Maps
  • GPS mapping
  • Mechanic
  • 2 or more experienced guides

Not Included

  • Airfare
  • Meals on off days
  • Souvenirs
  • 12% gratuity for guides, mechanics, volunteers and tour staff is not included, but greatly appreciated

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Special Note: Due to the length and cost of this tour, we ask that each registrant call the office staff personally and discuss the personal goals you desire to achieve from a tour of this magnitude. Prior to Registering, please read the following link to our special tour documents: Cross Country Bike Tour – Waiver and Release/ Safety Procedures