Getaway Weekend: Dewey and Rehoboth Beaches in Delaware

She was unapologetically herself, not once explaining herself to anyone. With jorts rolled up unevenly and hair gone astray, she was carefree. Maya produced her trademark happy head wiggles in the middle of a restaurant where others bring their best etiquette. On top of an umbrella ride, she molded quad chin faces because she knows she’s beautiful anyway. Kids under the age of 12 were betting their dollars when she excitedly joined in their game booth, knowing she could be like them at 30. Showing me around the place where she grew up spending routine summer vacations with her family had me riddled with admiration and such love. Last weekend, we ventured throughout Dewey and Rehoboth beaches in Delaware.

I put together the following sample itinerary which includes what Maya and I luxuriated in and recommend for your pleasure too.

Day 1 in Dewey Beach

1. If you prefer a quieter scene and more ample space for you and your company at the beach, Dewey Beach is your spot. There’s less noise, no boardwalk, and a relaxing atmosphere as compared to the crowded, lively Rehoboth Beach just minutes away.
2. If you’d rather not fuss about packing a picnic, you can head across the street to Grotto’s Pizza for a midday meal. They’re always running summer-long specials and hey, their pizza? Its a dreamy swirl in your mouth both metaphorically and literally.
3. After a heated, sandy day, head over to the patio bar right on the pier called Rusty Rudder just before dinner time. Find a suitable umbrella for shade and order your choice of a refreshing drink or two. They serve frozen strawberry daiquiris, a variety of margarita flavors, crushed alcoholic drinks, ice-cold beer and a plethora of appetizers to choose from. Sit back, slurp and sync to some live music coming from the adjoining performance stage.
4. After some refreshments and lively entertainment, go on a 10 minute walk down the main road until you arrive to Woody’s. If you want to be impressed by award-winning crab cakes through some casual dining in the evening, Woody’s got your back. Order the Crab Cake Platter as an entree which will give you two 6 oz. crab cakes at $33.50. It just might be your night to splurge on a pricey, delicious meal. I mean…we’re talking: Best of Dewey 5 years in a row by iDewey, Best of Delaware Crab Cakes & Best Restaurant in Dewey Beach by Delaware Today 2014-2017 and Best Crab Cakes by Coastal Style Magazine for the past 3 years.

Day 2 in Rehoboth Beach

Travel by the Jolly Trolley from Dewey Beach over to Rehoboth Beach, a sweet 7 minute ride. The trolley runs from 8am – 2am. The fare is $3.00/person one-way or $5.00/person round trip. If you’ve got anyone under 5 years old in your crew, they can hop on for just a buck! There are some trolleys that are wagonized behind a big van, some that are classics, and the rest are party bus style for late night trips. For your convenience, the fixed route of the jolly trolley is downloadable at the end of this post.

1. Hop off the trolley when you arrive to Rehoboth Ave. which meets the boardwalk and the busier scene offered at Rehoboth Beach. Take a stroll up and down the shopping district, going into whichever stores/venues you please. Keep an eye out for the alleyway strips such as Penny Lane Mall which are lined up with small, chic shops. Treat yourself with a snack and drink while you walk around. Popcorn. Fudge. Freshly-squeezed lemonade. All the deliciously classic tastes at the beach.
2. Just around the corner from the bustling shopping district is one of the funnest parts on the boardwalk: Funland! This classic game park is family-owned and was operated since the 1960s. It is nestled inside a large warehouse which opens back up to the sky inside where all the amusement rides are swirlin’, swingin’, and spinnin’. Two things you can appreciate here are the modest prices and the use of old-fashioned paper tickets awarded as tokens. A single ticket is only $0.40. If you want a discount, you can get a 50 or 100 ticket book that price tickets at just $0.36 or $0.30 respectively! Provided is a list of the rides available and the amount of tickets needed for each.
3. After spending all your money on the adrenaline-rushed action at Funland, walk up town to the Dogfish Head Brewings and Eats for dinner. In 2018, this location opened up a 36-seat patio that sits right next to lengthy transparent windows for views of the active brewery. Also, another neighbor to the location is the emporium if you feel you haven’t gotten enough of Dogfish. They sell apparel, canned & bottled drinks, and growlers to take home.
4. To wrap up your night, jot over to Royal Treat on Wilmington Ave. for a late night treat. You’ll see lines bursting out the front doors, steps, and into the sidewalk. This place ranks in the top 5 and 10 of Dessert and Best Places to Eat in Rehoboth Beach…you won’t be disappointed.

To see Maya immersed in her childhood pastime setting, I observed her appreciation of the childhood she had. Her innocence and playful spirit revealed themselves. It became apparent to me that she has a bucket of happy memories in stow.

I had the best time.