The Oldest Town In Delaware That Everyone Should Visit At Least Once

The history of the earliest settlement in Delaware is much like the Swamp Castle scene in Monty Python and the Holy Grail, where the King explains that he built his estate, and then it sank, and then he rebuilt it, and it sank again, and he built it a third time – and then it burnt down, fell over and again sank into the mud. But on the fourth time, it stood. The same can be said for Lewes.

The Dutch first settled in Lewes in June of 1631, turning it into a whaling and trading spot called “Zwaanendael.” A year later, a local tribe of Native Americans wiped out the settlers rather easily. The Dutch were hesitant to return, until Amsterdam laid claim to the area around Cape Henlopen to keep it out of British hands. This second settlement, in 1663, also lasted just one year before the English destroyed it, leaving nothing but rubble – and taking even most of the rubble for themselves.

The resilient Dutch gradually rebuilt the area around the Cape, and in 1673 the area was again attacked and burned down by soldiers from Maryland. England kept the area this time, until 1682, when all of Delaware was given to William Penn by the King of England. Penn renamed the settlement “Lewes,” and this time, the town stayed up. Come wander through this quaint, charming Delaware town to really feel like you’re a part of history, and a part of a life that the Dutch and English could have never imagined when they began to build it up.

Wikimedia Commons

You could easily spend an entire day wandering in and out of the shops and stores, window shopping or running up your bill.

Flickr / Lee Cannon

Mariners docking in front of a Lewes Landmark - Irish Eyes restaurant - is something you'll see every day in Lewes.

Advertisement

Flickr / Lee Cannon

The Lightship Overfalls is a floating museum dedicated to the history of the United States Lightship Program. It's absolutely fascinating and is a great thing to experience if you're interested in maritime history.

It's part of the Lewes Canalfront, at 219 Pilottown Rd, Lewes, DE 19958

Advertisement

Flickr / Lee Cannon

The Lewes Lifesaving Station is one of the stations along the Delaware coast that was responsible for helping stranded or distressed mariners, particularly in large storms. The building now stands as a tribute to the men whose orders said to go out, but never promised coming back.

Related Stories

There's No Attraction In The World Quite Like This One In Delaware

A Visit To This Delaware Town Will Make You Feel Like You've Traveled Back In Time

The Landmark Burger Joint In Delaware That Will Take You Back In Time

Flickr / Doug Kerr

Lewes is proud to be the "First Town in the First State," and the Zwaanendael Museum is a testament to the Dutch settlement.

You can find this amazing place at 102 Kings Hwy, Lewes, DE 19958.

Flickr / Doug Kerr

During the War of 1812, the British unsuccessfully tried to bombard Lewes. To this day, there's still a - you guessed it - cannonball lodged into the wall of the Cannonball House.

Visit this historic site at 118 Front St, Lewes, DE 19958.

Flickr / Melissa

This is one of the best State Parks in Delaware, for sure. With miles of trails, a World War II observation tower that can be climbed, the remnants of an abandoned World War II Fort that can be explored, and of course, the Ferry that takes you to Cape May, Cape Henlopen State Park is a place that could keep you occupied for a week!

Flickr / Mike Mahaffie

In the summer, Lewes is the swimming location of many people from all over the region. Soft sand, calm water, and well-kept beaches make this place a winner. Plus, it's only a short bike ride from Rehoboth Beach, where you can stuff your face with Thrasher's fries and Dolles' candy.

Have you visited Lewes? If not, you need to plan a day to visit this lovely, historic city! Maybe make it a stop on your next Delaware weekend road trip.