While we love to travel and explore new places, Lewes, Delaware is the summer destination we always come back to. Our oldest kid just turned eleven and this year marked our eleventh consecutive summer trip there. Lewes is picturesque, unpretentious, and provides variety – you can stroll to many local shops and restaurants, visit laid-back breweries, relax by the bay’s gentle waves, or enjoy the ocean beach’s surf. You can also easily drive to Rehoboth for more excitement. The tips below are based on our eleven trips, some of which were just the four of us and others with multi-generational family and friends.

The Practical Takeaways

• Lewes is roughly 3 hours from the Washington, DC region (though that all depends on the Bay Bridge traffic!). It is also accessible from New Jersey by way of the Cape May-Lewes Ferry, making it an easy destination to meet east coast family and friends in the middle. 
• Each of the Delaware beaches have its own reputation and vibe. We prefer Lewes because of its small town feel and the options it provides from shopping to its low-key bay. You do need to get in your car to go to the beach (it’s a 5 minute drive and $10 fee for out of state cars), so if you are seeking ocean waves everyday you may want to go further south to Rehoboth or Bethany.

Accommodations

We rent a house in-town every year. This can be done through VRBO, AirBnB, or Jack Lingo. Once we know who we are going with and how many bedrooms we will need we typically start the search in December. It can be pretty difficult to find a place for the summer once spring rolls around. Most houses require a week-long stay, though we have gone early enough in June when some allow half-week rentals. We have also gotten lucky with new rentals offering partial-week options.

Some of our friends and family have stayed at the Inn at Canal Plaza while we’ve been in Lewes – this option can be planned much closer to summer. 

Things To Do

Boat Ride with Cape Water Tours and Taxi: The Cape Water Tours and taxi company offers several great boat rides. If it’s your first time in Lewes I’d recommend the Eco-Tour or East End Lighthouse Tour to get your bearings. Our favorite boat ride offered is the sunset dolphin cruise – you see lots of dolphins against a beautiful backdrop. For all the boat rides you can bring food and drinks, making it a convenient excursion at any time of day.

Savannah Beach: In Lewes there are two options for the beach: the Bay or the Ocean. The Bay is at the end of Savannah Rd and free (except for parking). The sand is clean and the water is calm enough that kids can easily swim in without much fear. We love coming here in the evening for sunset swimming. The parking lot can fill up quickly between the hours of 11am-3pm, so plan to come before or after if you are driving.

Cape Henlopen State Park: We first fell for Lewes when staying in Rehoboth one summer and went to Cape Henlopen for a hike. We loved that the hike offered a range of experiences, including forest trails with deer sightings, to sandy beaches and ocean views with dolphins swimming in the distance. In addition to hikes, Cape Henlopen offers a beach with big ocean waves, endless bike trails, WWII fortifications, and a Nature Center. A favorite spot of ours is the “secret beach” (as my kids call it) at the end of the 0.5 mile Seaside Nature Trail. Note that the Henlopen main beach gets very crowded on weekends. 

Bike Rides: Lewes offers really great and relatively flat bike trails. Both of my kids learned to ride bikes in Lewes. In addition to biking in Cape Henlopen, we enjoy taking the Georgetown-Lewes Trail from the canal to Station on Kings. Many of the houses we have stayed in have included bikes, but we have also rented from Seagreen and Lewes Cycle Sports. 

Farmers Market: The Saturday morning farmer’s market in Lewes is huge and always fun to visit. We like going at the beginning of our trip to pick out meat and veggies to grill. Anything we’ve forgotten or can’t find we then supplement with a trip to our favorite in-town grocery, Lloyd’s, which carries many of the local farm fresh goods you’d find at the market. There is also a smaller farmer’s market on Wednesday mornings in the Crooked Hammock parking lot. 

Second Street Shopping: One of the reasons we love Lewes is the shopping along Second Street. While it’s only a quaint two block stretch, the stores offer a bit for everyone. A few of our favorites include Deanna’s & Piccolino, Shorebreak, Gypsy Myst, the Lewes Puzzle Store, and, of course, Kids Ketch (a trip to Lewes is not complete without multiple trips to this toy store).

Lewes Canalfront Park and Playground: It was hard to believe that on this year’s trip we never went to the playground. For ten years, this was often our first stop each morning as we took turns pushing the kids in the swings and playing tag on the Waterfront Park lawn. In the past we’ve also brought takeout to the park to eat dinner at the picnic tables, which always seemed magical in the setting along the canal.

Outside of Lewes

Rehoboth: As a kid and through my 20’s, Rehoboth was my summer destination. The eighteen-year-old in me can’t believe we stay in Lewes now and not Rehoboth – but alas, I’ve grown up and now enjoy some quiet. That being said, a summer vacation at the Delaware beaches is not complete without a trip to Rehoboth and, more specifically, Funland. Being tall enough to ride the Sea Dragon is a rite of passage, as is being brave enough for the Haunted Mansion (which my son finally conquered this summer). No matter how many trips to amusement parks we’ve taken, including Disney World and Universal Studios, nothing takes the place of Funland.

In addition to Funland, there are two other places we always go to: 1) Louie’s Pizza (I think it’s the best…others may not, but my nostalgia for this pizza outweighs all other factors); and 2) Browseabout Books (as far as independent bookstores go, it’s up there with Square Books for me). 

Once we’ve checked off Funland, Louie’s, and Browesabout, we spend the rest of the time meandering through shops on Rehoboth Avenue and along the boardwalk. There are so many great restaurants too – we often enjoy Claws Seafood House to pick apart crabs or the rooftop garden at the Cultured Pearl.

Kayaking in Rehoboth Bay: To escape the beach crowds, we enjoy calm kayak excursions at Rehoboth Bay in Dewey. Before or after kayaking, I’d recommend lunch at Nalu.  

Mini Golf: There are plenty of places to play mini golf along Route One. On our most recent trip we went to the Midway Speedway Park, which I hadn’t been to since high school. It turned out to be a fun course that provided some shade as two of the holes are inside a “volcano.” After golf, my kids enjoyed the go-kart track.  

Places to Eat

For a small town, Lewes offers so many restaurants and we’ve tried almost all of them. For a nicer meal I’d recommend Agave, Raas, or Heirloom. With kids, the following are always on our list:

Breweries: There is always a debate on which we like better: Big Oyster or Crooked Hammock. Both have great food and beer, but what really makes these two places attractive for families are the playgrounds and expansive kid areas in the back. You can take your time and relax at either. Next summer we are excited to try Lewes Brewing Company (it opens in late 2024).

Olive and Oats: The Cafe Panini sandwich is one of my favorites – at least once a summer I get it to go and eat it at the beach or Canalfront Park. 

Rosenfeld’s: As former New Yorkers, we are hard to please when it comes to finding a decent Jewish deli. Rosenfeld’s meets the challenge – their corned beef sandwich and matzoh ball soup is just as good as any of my favorite places in New York. 

Touch of Italy: Year after year, for our first night in Lewes we order pizza and cannoli cake to-go from Touch of Italy. It’s tradition.

King’s Ice Cream: Another tradition is standing in an epic line for ice cream at King’s. I have so many cherished photos and memories of ice cream running down my kids faces while sitting outside here.

Nectar: This is a favorite for its juices and breakfasts – get here when it opens at 8am, otherwise you’ll be waiting for a while.

Kindle: We’ve never had a bad meal at Kindle – in pulling up the menu I tried to see if I had a favorite, but honestly, everything is good. Unfortunately they don’t take reservations, which is often a barrier to eating here with a group.

A Few Extra Tips

• In case you’re wondering, it’s pronounced “loo-is”
• Lewes is very dog-friendly and in the mornings and evenings you’ll find many families and their dogs at the Bay. In fact, our own dog is named Louie in recognition of Lewes and Louie’s Pizza – and he’s made dog-friends also named Louie there! 

• We plan our trips over to Rehoboth during the week when there is lighter traffic on Route One. If you can, avoid Route One at all costs during the weekend – Lewes and Rehoboth are only 5 miles apart, but with traffic it can feel like 50 miles.
• On days where the weather isn’t the best for the beach we’ve enjoyed visits to the Lavender Fields, Dogfish Head Brewery tour, and Prime Hook National Wildlife Park. There are also the tax-free outlet malls along Route One and if it’s raining and you’re desperate for kids to burn off energy there is Shell We Bounce Trampoline Park.
• Looking for a summer vacation with more adventure? Check out my post about our Southwestern summer road trip!