Blake Walsh

16 Best Things to Do in Deale, MD

  • Published 2022/09/07

Categorized as a census-designated place or CDP, Deale is a bustling Chesapeake Bay community in Anne Arundel County, Maryland.

With Rockhold, Parker, and Carrs creeks, Deale is surrounded almost entirely by water.

The area’s first white settlers were the Puritans, who arrived in 1655 from Virginia.

Formerly called Herring Creek, Deale was primarily known as a farming community until the late 1800s.

Its remarkable transformation from a farming to a fishing community was mainly due to the bountiful oyster supply in Herring Bay.

Today, Deale is home to many marinas and fishing charters.

As such, it is a popular destination for boaters and sport-fishing enthusiasts.

Here are the best things to do in Deale, Maryland:

Check-in at Anchored Inn at Hidden Harbour

Anchored Inn at Hidden Harbor is a three-star hotel on Cabana Boulevard, right in the heart of Deale.

This boutique-style inn is hard to miss, thanks to an old anchor displayed right outside the building.

Moreover, this relatively tiny hotel boasts a large outdoor pool where you can swim or relax by the pool.

Their free Wi-Fi internet access allows you to keep tabs on work online while on vacation.

Stay in one of their balcony rooms and be greeted by stunning waterfront views of Rockhold Creek.

You can even check in with your pets in this hotel, as it is also pet-friendly.

These outstanding amenities and more make Anchored Inn at Hidden Harbor the perfect staycation spot in Deale.

Chill at The Boathouse

The Boathouse is one of the most popular hangout joints in Deale.

As its name implies, the bar is built on an old boat.

Moreover, the building is made almost entirely of wood planks, reminiscent of an old harbor warehouse.

The Boathouse’s main draws are its food, drinks, and overall chill atmosphere, complete with live music performances.

You can pair their delicious dishes with an ice-cold beer or one of their signature cocktails.

Feast on Seafood at Skipper’s Pier

Located along Drum Point Road, Skipper’s Pier is one of Deale’s most famous eateries.

Boasting a wide array of food and drink selections, the restaurant ensures they have something that will suit even the pickiest taste buds.

Their seafood specialties, like crabs, shrimp, and oysters, headline their impressive menu.

Meat lovers will love Skipper’s Pier for its delicious steak, burgers, and chicken.

Satisfy your cravings for sweets when you try their tasty desserts.

You can wash them all down with their refreshing non-alcoholic and alcoholic beverages.

As a pleasant bonus, you can indulge in a sumptuous meal while enjoying the scenic views of Herring Bay.

Enjoy the Amenities at Shipwright Harbor Marina

Several marinas dot Deale’s extensive waterways.

Shipwright Harbor Marina stands out as one of the best, thanks to its neat extra amenities.

The marina features 250 deep-water slips, ranging between 20 to 78 feet.

Its amenities include a saltwater pool and picnic areas with grills, which are always perfect for cookouts.

Moreover, Shipwright Harbor Marina provides complimentary kayaks and bikes, which you can use to explore Deale.

Satisfy Your Sweet Cravings at Sandy Pony Donuts

A tiny donuts stall originating from eastern Virginia, Sandy Pony Donuts is fast becoming popular in the area thanks to its expansion in Deale.

Considered among the tastiest in the region, their donuts are always served hot and fresh.

With over 25 donut flavors on their menu, you’ll need a couple of boxes to enjoy them all.

Their thick and creamy smoothies and bubble tea match perfectly with their fluffy donuts.

If you’ve got a sweet tooth, your Deale itinerary must include Sandy Pony Donuts on Bay Front Road.

Go Antique-Hunting at Vintage By The Bay

Vintage By The Bay is Deale’s go-to spot for antique and bargain hunting.

The shop on Deale Road sells old wooden furniture like dressers, side tables, and cabinets.

They also have home decor and other interesting knickknacks.

Their decorative artwork pieces are also a great addition to any room.

Moreover, they also accept commissions for custom jobs like adding paintworks onto items.

Whether you are a collector or want something as a souvenir from your visit to Deale, you can always grab something nice at Vintage By The Bay.

Roam around Deale with Solo Cup Water Taxi

Water makes up a significant portion of Deale’s area and economy.

One of its most important waterways is Rockhold Creek, which cuts through the community’s busiest and most populated part.

These features make Solo Cup Water Taxi a unique and fun way to commute around these locales.

The water taxi is perfect for group tours and is big enough to accommodate ten adult passengers.

You can cruise along the creek and other nearby waterways.

You can also use the taxi to reach many of Deale’s restaurants and other bayside attractions.

A great way to explore Deale, riding the Solo Cup Water Taxi is an experience everyone must try.

Enjoy Water Activities with Chesapeake Paddle Sports

As a bayside community, Deale is the perfect spot for fun water activities like paddling and kayaking.

Chesapeake Paddle Sports allows you to enjoy these with their paddle board and kayak rentals.

You can also avail their double kayaks and two-person pedal boats.

Moreover, they give stand-up paddle (SUP) board lessons for beginners and other SUP techniques like yoga and fitness.

They also hold a four-day summer camp for kids and other special events.

You can take their kayak eco-tour and enjoy the scenic views of Deale from Rockhold Creek.

Chesapeake Paddle Sports has everything you need for fun and memorable water activities.

Dine at Cappy’s

A family-owned business, Cappy’s is one of the newer restaurants in Deale.

Along with seafood specialties, they are famous for their tasty fried chicken and side dishes.

Health-conscious diners will also be delighted by their vegan and vegetarian options.

The restaurant’s location and layout exude a quiet and relaxing vibe.

Even when packed, it doesn’t feel crowded at all with its neatly-spaced tables.

On top of great food and a calm atmosphere, diners will also be treated to great views of Herring Bay.

Cappy’s is located on Deale Road.

Go Sport Fishing with Wild Goose Charters

Wild Goose Charters stands out as one of the best fishing charters in Deale.

Its namesake 46-foot vessel boasts speed, comfort, and reliability.

With safety as the utmost priority, it is well-equipped with modern devices.

Manned by a highly skilled crew, the boat can carry up to 26 people.

It also features enclosed bathroom facilities.

The charter’s Trophy Striped Bass Fishing and Bottom Fishing will excite any angler.

However, if you’re not in the mood for fishing, you can simply cruise the bay in style.

Sail away with Wild Goose Charters for a thrilling and memorable fishing experience.

Enjoy Japanese Food at Deale Umai Sushi House

Thanks to Chesapeake Bay’s abundant culinary resources, there’s seemingly no shortage of seafood restaurants in the region.

With its specialty in Japanese cuisine, Deale Umai Sushi House stands out among them.

This hole-in-the-wall restaurant on Deale Road prides itself on using fresh ingredients and seafood from the bay.

On top of their signature sushi, the restaurant also serves authentic Japanese food like tempura, gyoza, teriyaki, and yakisoba.

They also serve flavorful Korean food like bibimbap, bulgogi, and japchae.

If you’re looking for a different Chesapeake dining experience, Deale Umai Sushi House will satisfy your palate.

Other Things to Do Nearby

Explore Jug Bay Wetlands Sanctuary

Boardwalk at Jug Bay Wetlands Sanctuary

StompingGirl /

Just 10 miles west of Deale, you will reach the Jug Bay Wetlands Sanctuary.

This pristine nature preserve covers a massive 1,700 acres area.

Wetlands, forests, grasslands, and plains comprise most of its vast terrain.

Daytime view of Jug Bay Wetlands Sanctuary

ForestSeasons /

With its sprawling 19 miles of trails, the sanctuary is also a popular destination for outdoor adventurers.

As home to many migratory birds and small animals, you will also enjoy wildlife-watching in this paradise.

A beautiful tree at Jug Bay Wetlands Sanctuary

ForestSeasons /

Moreover, the sanctuary also hosts field trips and private group programs.

These activities allow visitors to gain a deeper understanding of the importance of preserving the environment.

Jug Bay Wetlands Sanctuary is an excellent place to immerse yourself in nature.

A butterfly at Jug Bay Wetlands Sanctuary

StompingGirl /

Go for Outdoor Adventure at Franklin Point State Park

Franklin Point State Park is located in Shady Side, about 5 miles northeast of Deale.

The state park covers an area of 447 acres.

Its landscapes comprise mainly marshlands, forests, and grassy plains.

You can trek along the park’s marked trail, traversing these natural terrains.

Enjoy amazing views of Flag Pond as you hike along the wooded trails.

Home to many birds and small animals, Franklin Point State Park is also a perfect location for wildlife viewing.

Visit Greenstreet Gardens

A quick eight-minute drive west of Deale in Lothian, and you’ll reach Greenstreet Gardens.

This botanical center is famous throughout the region for its beautiful flowers and other attractions.

Gardening enthusiasts will have a field day browsing its vast array of annuals, perennials, herbs, shrubs, and trees.

The center also features a sprawling corn maze.

Its petting zoo allows visitors to interact with farm animals.

Moreover, its highly-anticipated Fall Festival draws many visitors each year.

With all these fun features, Greenstreet Gardens isn’t just a gardener’s paradise but also an all-in-one place for family recreation.

Dock and Relax at Herrington Harbor South

Herrington Harbor South is a beautiful marina located on North Beach, 10 miles south of Deale.

With its 600 boat slips, this marina is one of the largest in the area.

On top of lodging accommodation, it’s also packed with other great amenities.

You can play and enjoy on its tennis, pickleball, and basketball courts, along with its fitness gym and a water fitness facility.

There’s also a picnic and playground area.

Its Olympic-size and kiddie swimming pools are a perfect way to cool off.

Moreover, you can swim or sunbathe at the marina’s private white sand beach.

For postcard-worthy views, you can walk to nearby Herrington on the Bay, considered by many as one of Maryland’s most beautiful wedding venues.

With its lovely amenities and stunning views, Herrington Harbor South isn’t simply a marina but also a great vacation spot.

Learn How to Sail at The Sailing Academy

A premier training center in Anne Arundel County, The Sailing Academy is located in Tracys Landing, a stone’s throw away from Deale.

It offers course categories for every skill level, from beginner-friendly to advanced.

Moreover, each category is further broken down into more specific courses for more focused learning.

Their single-session Try Sailing course is the perfect way to introduce anyone to the exciting world of the sport.

Those who seek certification can also take advanced courses.

Carrying decades of experience under its belt, its team of professional instructors assures you that you only get the best quality training.

An excellent way for both budding and experienced sailors to level up their skills, The Sailing Academy will also help jump-start your love for sailing.

Final Thoughts

As a beautiful seaside community with fantastic views of Herring Bay, Deale is a top sailing destination in the Chesapeake Bay area.

Its great restaurants, neat accommodations, and fun activities make it a highly enticing vacation spot.

Deale’s proximity to many nature parks also makes it a perfect destination for outdoor enthusiasts.

Try all the best things to do in Deale, Maryland, and enjoy a worthwhile experience.

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