Join us for a historical and scenic bike tour of four of the states first admitted to the Union in 1776: Pennsylvania, New Jersey, Delaware and Maryland. We meet in Philadelphia and start our ride on the Perkiomen and Schuylkill River Trails, riding through rural Penns Woods, Valley Forge, and then back into the City of Brotherly Love. Next up is the Jersey Shore, cycling through barrier islands from Ocean City to Cape May. Crossing over to Lewes, Delaware by ferry, we explore the First State and Maryland on country roads. We finish the trip on the C&D Canal Trail to arrive in New Castle, one of the most historic towns on the Delaware River.
Independence Hall
Valley Forge National Park
Schuylkill River Trail
Jersey Shore
Scarborough Inn
Hotel Rodney
Day 1: We meet in Philadelphia and shuttle to the the 20-mile Perkiomen Trail, which follows the beautiful Perkiomen Creek from Oaks to Green Lane Borough. For most of its length, the “Perky,” as it is known by many, uses the former rail bed of the Perkiomen Line of the Reading Railroad. It passes through the historic villages and towns of Arcola, Collegeville, Schwenksville, Spring Mount, and Green Lane.
After a quick stop at the John James Audubon Center and the first home in America of the famed artist and naturalist, we hop on the Schuylkill River Trail (SRT). A detour off the SRT takes us to Valley Forge National Historical Park, the site of the 1777-78 winter encampment of George Washington’s Continental Army.
We finish the day riding along the Schuylkill River past the suburbs of Bridgeport, Conshy, and Manayunk. Our ride concludes in Philly, founded in 1682 by William Penn and full of colonial history and modern vibrancy. Dinner is together tonight overlooking the Delaware River.
Day 2: We begin our day touring Independence Hall, where the Declaration of Independence and U.S. Constitution were signed. Here we explore the West Wing and Signers’ Garden, with exhibits including the original founding documents. Then we make our way to the Betsy Ross House, Liberty Bell, and Old City District.
Crossing into New Jersey, we start today’s ride in the Pine Barrens, traversing country roads in South Jersey on our way to Ocean City. Known for its family-friendly boardwalk, sandy beaches, and amusement piers, Ocean City is part of the string of barrier islands that protect New Jersey’s mainland from the Atlantic. These narrow, shifting islands have long drawn visitors seeking summer escapes, while also playing a crucial role in coastal ecology.
We spend the night at the historic Scarborough Inn, which is almost as old as the town itself. It has a blend of nostalgic charm and modern comfort and is owned and operated by lifelong locals. Dinner is on your own tonight in this quaint seaside town.
Day 3: After a wonderful breakfast at the Inn, we continue riding south along the New Jersey coast, arriving in Cape May, America’s oldest seaside resort. With its charming Victorian architecture and historic lighthouse, Cape May offers both relaxation and history. Birdwatchers flock here during migration seasons, as the area is one of the East Coast’s premier birding locations. Tonight our accommodations are just steps away from the beach. We enjoy dinner together in a town known for its superb seafood.
Day 4: Begin the day with a sunrise stroll on the beach and breakfast. Then pedal out of town, stopping to visit Cape May Point State Park with the Cape May Lighthouse, Birding Observation Deck, and Fort Miles Battery 223. Next up is Sunset Beach with views of the Delaware Bay – you might find a Cape May Diamond here!
The Cape May-Lewes Ferry takes us across the Delaware Bay so we can cycle through Cape Henlopen State Park. William Penn, an early leader of Delaware, decreed the park one of the first public use lands in the Thirteen Colonies in 1682.
Lewes, aptly called “the first town in the first state,” was established by Dutch colonists in 1631 and called Zwaanendael or “Valley of the Swans.” It is known for its shops, restaurants, spas, antiques, and some of the best outlet shopping on the East Coast, and it’s all tax-free!
After checking into the Hotel Rodney in the historic downtown area, you have time to explore and have dinner on your own.
Day 5: Today we shuttle inland to visit Bombay Hook National Wildlife Refuge by bike. The refuge, located along the coast of Delaware Bay, protects the largest remaining expanses of tidal salt marsh in the mid-Atlantic region. It is mostly marsh but also includes freshwater impoundments and upland habitats managed for migratory birds and other wildlife along the Atlantic Flyway. We bike through eight miles of the refuge, passing observations towers and stopping at a wildlife boardwalk.
Next, we head westward on country roads to reach Chesapeake City, MD. Founded in the early 19th century, this historic canal town was built around the engineering marvel of the C&D Canal, which still connects the Chesapeake Bay and the Delaware River. Today, the town is known for its restored 19th-century homes, waterfront dining, marina, and small-town charm. Tonight, we celebrate an incredible week of cycling and sightseeing with a final dinner together.
Day 6: Our final ride is on the C&D Canal Trail into New Castle, DE, one of the most historic towns on the Delaware River. Founded in 1651, it has changed hands among the Dutch, Swedes, and English, leaving behind a unique architectural legacy. The cobblestone streets, colonial courthouse, and stately homes make New Castle feel like a step back in time. At the end of our ride, we take a private tour of the Read House & Gardens, a significant early example of high-style Federal period architecture.
This is truly a fitting end to our journey, rich in history, culture, and coastal beauty. We return to Philadelphia, where we say our goodbyes!
Minimum Age
5 Breakfasts | 5 Lunches | 3 Dinners
PP Double Occupancy
Single Supplement*
Standard Bike Rental
*This is required if you are traveling solo or if you are traveling with someone but require separate beds.