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East Coast Greenway – Segment II Bike Tour

Ride through the roots of American history on a scenic journey from colonial towns to Southern charm, exploring battlefields, greenways, and cultural shifts along the way.

Average Climate

No upcoming dates are currently available for this trip.

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Double Booking TBD

Single Booking TBD

Roommate Rebate TBD

Trip Type

Cycling

Difficulty Level

1

Trip Length

17 Days, 16 Nights

Distance

756 Miles
1216.7 Kilometers

Meeting Time

12 PM airport pickup, 4 PM Manhattan

Drop-off Time

9 AM Raleigh departure

Assembly Point

New York, NY

Inclusions

One pickup time at each New York area airport will be provided by Timberline. Not Included: Airfare to New York City area; Alcoholic Drinks; Guide Gratuity

Lodging Highlights

  • Vandiver Inn
  • Garden Inn Annapolis
  • Capitol Hill Hotel
  • Clarion Point on the Lake
  • Longleaf Hotel

Have questions? We’re here to help! Call us at 303-664-8388 or reach out online.

Contact For Details

The East Coast 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. 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.

Greenway Cycling: A Ride Through History

Segment 2 of our east coast bike ride is the historical section. We travel through the states and cities that were so instrumental in creating our nation.  We will ride past battlefields, government sites, through 7 of the first thirteen colonies, five capital cities, and countless historical markers.  Along the way, we will ride several canal towpaths, more than 60 greenways, and a surprising number of quiet miles on country roads.  Our layover day is spent in Annapolis, MD, where you can choose to relax on the beach, shop in town, stroll the historic neighborhoods, or even charter a boat to explore Chesapeake Bay.  As the climate cools towards winter, we cross the Mason-Dixon line, pushing ever farther south.  Words, accents, food, attitudes, drivers, and humidity will all make that north to south transition.  We end our tour in Raleigh, the capital city of North Carolina, and one of the South’s most vibrant, eclectic cities – where eclectic meets traditional and historic meets modern.

NOTE: Sign up for as many segments as you want.  Multiple segment bookings get an additional cumulative 5% discount for each segment.

Explore the entire Greenway Map

ITINERARY

Day 1: Orientation - New York City, NY

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Accommodation: Vandiver Inn - Garden Inn Annapolis - Capitol Hill Hotel - Clarion Point on the Lake - Longleaf Hotel

Meals: Breakfast, Lunch, Dinner

Day 2: New York City - NY Waterway Ferry - Newark - Rahway River Parkway - New Brunswick, NJ (47 miles)

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Accommodation: Vandiver Inn - Garden Inn Annapolis - Capitol Hill Hotel - Clarion Point on the Lake - Longleaf Hotel

Meals: Breakfast, Lunch, Dinner

Distance: 47 miles

Day 3: New Brunswick - Delaware & Raritan Canal Towpath - D&L Trail - Bristol, PA (53 miles)

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Accommodation: Vandiver Inn - Garden Inn Annapolis - Capitol Hill Hotel - Clarion Point on the Lake - Longleaf Hotel

Meals: Breakfast, Lunch, Dinner

Distance: 53 miles

Day 4: Bristol - Philadelphia Fairmount Park - Schuylkill River Trail - Wetland Loop Trail - Northern Delaware Greenway - Wilmington, DE (61 miles)

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Accommodation: Vandiver Inn - Garden Inn Annapolis - Capitol Hill Hotel - Clarion Point on the Lake - Longleaf Hotel

Meals: Breakfast, Lunch, Dinner

Distance: 61 miles

Day 5: Wilmington - Jack Markell Trail - Newcastle, DE - James F Hall Trail - Elkton - Havre de Grace, MD (51 miles)

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Accommodation: Vandiver Inn - Garden Inn Annapolis - Capitol Hill Hotel - Clarion Point on the Lake - Longleaf Hotel

Meals: Breakfast, Lunch, Dinner

Distance: 51 miles

Day 6: Havre de Grace - Bel Air - Torrey C Brown Trail - Cockeyesville (48 miles)

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Accommodation: Vandiver Inn - Garden Inn Annapolis - Capitol Hill Hotel - Clarion Point on the Lake - Longleaf Hotel

Meals: Breakfast, Lunch, Dinner

Distance: 48 miles

Day 7: Cockeyesville - Jones Falls Trail - Baltimore - Baltimore & Annapolis Trail - Annapolis, MD (50 miles)

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Accommodation: Vandiver Inn - Garden Inn Annapolis - Capitol Hill Hotel - Clarion Point on the Lake - Longleaf Hotel

Meals: Breakfast, Lunch, Dinner

Distance: 50 miles

Day 8: Layover day - Annapolis, MD

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Accommodation: Vandiver Inn - Garden Inn Annapolis - Capitol Hill Hotel - Clarion Point on the Lake - Longleaf Hotel

Meals: Breakfast, Lunch, Dinner

Day 9: Annapolis - Washington & Annapolis Trail - Metropolitan Branch Trail - Washington, D.C. (57 miles)

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Accommodation: Vandiver Inn - Garden Inn Annapolis - Capitol Hill Hotel - Clarion Point on the Lake - Longleaf Hotel

Meals: Breakfast, Lunch, Dinner

Distance: 57 miles

Day 10: Washington D.C. - National Mall - Mount Vernon Trail - Occoquan Bay National Wildlife Refuge - Aquia, VA (57 miles)

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Accommodation: Vandiver Inn - Garden Inn Annapolis - Capitol Hill Hotel - Clarion Point on the Lake - Longleaf Hotel

Meals: Breakfast, Lunch, Dinner

Distance: 57 miles

Day 11: Aquia - Fredericksburg - unencumbered road riding - Ashland, VA (65 miles)

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Accommodation: Vandiver Inn - Garden Inn Annapolis - Capitol Hill Hotel - Clarion Point on the Lake - Longleaf Hotel

Meals: Breakfast, Lunch, Dinner

Distance: 65 miles

Day 12: Ashland - Richmond - Reedy Creek Trail - Chester - Petersburgh, VA (51 miles)

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Accommodation: Vandiver Inn - Garden Inn Annapolis - Capitol Hill Hotel - Clarion Point on the Lake - Longleaf Hotel

Meals: Breakfast, Lunch, Dinner

Distance: 51 miles

Day 13: Petersburgh - Dimwiddle - Tobacco Heritage Trail - La Crosse, VA (68 miles)

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Accommodation: Vandiver Inn - Garden Inn Annapolis - Capitol Hill Hotel - Clarion Point on the Lake - Longleaf Hotel

Meals: Breakfast, Lunch, Dinner

Distance: 68 miles

Day 14: La Crosse - Dick Cross Wildlife Management Area - John H Kerr Reservoir - Clarksville, VA (41 miles)

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Accommodation: Vandiver Inn - Garden Inn Annapolis - Capitol Hill Hotel - Clarion Point on the Lake - Longleaf Hotel

Meals: Breakfast, Lunch, Dinner

Distance: 41 miles

Day 15: Clarksville - Oxford - Stern - Durham, NC (60 miles)

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Accommodation: Vandiver Inn - Garden Inn Annapolis - Capitol Hill Hotel - Clarion Point on the Lake - Longleaf Hotel

Meals: Breakfast, Lunch, Dinner

Distance: 60 miles

Day 16: Durham - American Tobacco Trail - White Oak Creek Greenway - Rocky Branch Trail - Raleigh, NC (47 miles)

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Accommodation: Vandiver Inn - Garden Inn Annapolis - Capitol Hill Hotel - Clarion Point on the Lake - Longleaf Hotel

Meals: Breakfast, Lunch, Dinner

Distance: 47 miles

Day 17: Raleigh - transition day

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Accommodation: Vandiver Inn - Garden Inn Annapolis - Capitol Hill Hotel - Clarion Point on the Lake - Longleaf Hotel

Meals: Breakfast, Lunch, Dinner

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