posted on November 21st, 2016

Colonial cruising

Thanksgiving honors America’s early settlers and their first feast with the Native Americans, so to get in the mood for giving thanks, why not take a little historically refreshing road trip to remind you of America’s beginnings?

While most of the trails on this epic colonial road trip were made long-ago by horse drawn carriages and footpaths, nowadays, they’re paved with splendid views that will take you swooping through historical villages, haunting battlefields, and heartrending monuments. Not to mention these colonial routes boast a barrage of rainbow-leaved forests this time of year — ideal for autumn admirers.

So, in the spirit of the first Thanksgiving, fasten your bonnet and (swash)buckle up, we’re pulling out all the puritanical pit stops.


The very beginning is always a good place to start — in good ol’ Plymouth, Mass. You may have heard of this one boat called the Mayflower? It landed here. And of course there’s Plymouth rock. However, there’s a lot more to Plymouth than just a rock.

Start your journey in Plymouth on route MA-3a also known as Old King’s Highway. Check out where the very first Thanksgiving was held on Plimoth Plantation, then head over to The Pilgrim Hall Museum which contains tons of colonial artifacts.

If you’re not keen on hiking up your breeches to get out of the car, that’s okay — the Great King’s Highway exhibits incredible scenery you can enjoy through the windshield. If you continue your cruise down south, in just a short time you’ll be wrapping around the kingly, sparkling Cape Cod. It’s richly historic, green, and stippled with nautical vistas all the way out to Cape Cod Bay. This route also reveals an impressive glimpse into New England village life, plus some great antiquing. Huzzah!



Once you’re done on the Cape, caravan down to Connecticut town. Take the quiet, historic, and tranquil CT-169 from Old Norwich to Woodstock. This road winds through old colonial homesteads, stone walls, fields, and quaint town greens. This route will easily take you time traveling right back to 18th century colonial America. Tip your flat-topped hat and give a “Good morrow” to the townspeople you pass along the way.

If all the time traveling has worked up your appetite, the historic Golden Lamb Buttery is just around the river bend, about 40 miles away. It’s the perfect place to pig out like the pilgrims did. It’s a regal, bright, red barn that sits on a 1,000-acre field, chock full of stone walls, gardens, woods, ponds, and history. The restaurant serves rustic dishes like chateaubriand, duckling, and rack of lamb; it even includes homages to authentic pilgrim fare like smoked mussel bisque. You might have to loosen your waistcoat before hopping back in the car.

New York

Next up, the Big Apple. New York City is brimming with colonial history. Take a careful cruise from Connecticut down into the heart of NYC by way of the CT-8 S and CT-15 S. Some of the coolest colonial digs in New York City include famous streets, parks, churches, and taverns.

You might want to start with a voyage down one of the oldest streets in the city, Wall Street. You’ve definitely heard of it, but did you know it’s named after an actual wall? The wall ran along the border of the early Dutch colony, New Amsterdam. That was like, 300 years before the stock market even existed!

Next, get out of the car for some fresh air. Let the history-soaked soil of New York’s oldest park seep into your stockings as you frolic in the grass of Bowling Green Park. The park was established in 1773, and the original iron fence erected in 1760 still surrounds it. In 1776, after hearing the Declaration of Independence, a crowd tore down the statue of King George in the park’s center, then cut the statue into pieces and melted the pieces into bullets for the Continental Army. The ornaments from the top of the fence were also cut off and melted into bullets — you can still see the irregular points from their removal. If that doesn’t ruffle your revolutionary feathers, I don’t know what will.


Take the 95 from New York City down into Philadelphia. The history in Philly is bountiful. From the Liberty Bell, to Independence Hall and, of course, a museum for the man who made turkeys famous in the first place — Benjamin Franklin.


After you’ve soaked up all the Philadelphian history you can absorb, make your way to the Amish Village in Lancaster, PA, by way of the I-76 W. This beautiful route is comprised of picturesque hills, cozy cabins, babbling brooks, and tilled farms with meadows. Travel back in time, until you finally arrive there, in the Amish village. There’s nothing like actual horse-drawn carriages, and no electricity or Internet to really hone in on that historic, colonial vibe. Not to mention the food is incredible. Visit Katie’s Kitchen for an authentic Amish dining experience. Pass the rye bread, please.


Driving through Maryland this time of year is a leaf peeper’s dream come true. Be dazzled by the autumn gold and rust-colored leaves along Maryland’s scenic byways. Take the US-30 W from Pennsylvania to land yourself in Baltimore, MD. It’s a quick and beautiful hour-and-a-half jaunt. From here you’ll follow the trail of British troops as they fought their way up the Chesapeake Bay and feel for yourself the bursting inspiration for the “Star-Spangled Banner.”

Take the MD-895 all the way down to Bladensburg, Maryland. There are historical stops all along the way, including The Star Spangled Banner Flag House, Fort McHenry National Monument and Historic Shrine, the Riversdale House Museum, and the beautiful Battle of Bladensburg Visitor Center and Waterfront park. Oh, say can you see all the pretty leaves?


Time to pay homage to our forefathers in Virginia. Head over to Mount Vernon where the man, the myth, the legend — George Washington himself — once resided. From Washington County, MD take the I-270 S to Mount Vernon where you can explore the 400-acre plantation and 21-room home of America’s first president.

Cross another forefather off your list by heading to Monticello in Charlottesville, VA by way of the I-95 south. Monticello was the sprawling mansion of Thomas Jefferson and provides a glory-filled glimpse into the life and times of one of America’s first great renaissance men.

Once you get tired of exploring old, huge mansions, you can finally head down to colonial Williamsburg, Jamestown, and Yorktown, by way of the I-64 E. Here you get to walk in the footsteps of the very first colonists in a recreated colonial town. You can even visit the first permanent English settlement in the new world, Jamestown, settled in 1607.


Thither you are, traveler. Fare thee well on your journeys, and I wish thee cheer on the day of your autumn harvest feast. Let us be thankful for the the early settlers who made the celebration of giving thanks a tradition.

Andi Ferraud is a Content Specialist at Turo. She’s a quirky writer with an eye for design. She loves sharks, spontaneous adventures, and horror movies.