Hit the beach at Herrington Harbor South.

Weekends on the Water: Deale, Maryland

Join CBM for a trip to Deale, Maryland. It may be one of the best-kept secret boating locations on the Bay with plenty of opportunities for docking and dining.

Fast facts

  • Located 15 miles south of Annapolis and 30 miles north of Solomons
  • Established in 1655
  • Home to the largest amount of deep-water, protected boat slips on the Bay

What Makes It Unique

Chesapeake Paddle Sports offers SUP rentals and tours.

Herring Bay is the location of choice for boaters who live in the Washington D.C. area. Once you get there, you are smack in the middle of the Bay, which means easy trips to Eastern Bay and St. Michaels as well as the Choptank River and Oxford or Cambridge. And of course, all those lovely fishing grounds will be right there, which makes Herring Bay a convenient destination as well as a central starting point. A down-home vibe and array of quirky dock bars makes it great place to spend a weekend as well.

Getting There

By boat

The channel entrance into Herrington South’s basin is straightforward and deep, but on the other end, the short section of channel from the Rockhold Creek breakwater to markers 8 and 9 is narrow and can be crowded on weekends and shallow in spots to about 5 or 6 feet at dead low tide. At markers 12 and 13, the channel for Herrington North splits to port while the main channel continues north then northeast to reach all the other marinas and the dock bars.

Coming up Rockhold Creek channel, you’ll find Skipper’s Pier Restaurant and Dock Bar to starboard, followed by Paradise Marina to starboard and then Shipwright Harbor Marina’s extensive docks to port. Rockhold Creek Marina is past that to port, and you continue on to Happy Harbor restaurant. Past the Deale Road Bridge, which has a vertical clearance  of 14 feet, lies Harbour Cove Marina, a popular location for smaller boats with shallower drafts, and finally Hidden Harbour, home to the Anchored Inn.

By car

To get to southern Anne Arundel County, take Rt. 2 south from Annapolis, or take Rt. 4 east from Washington D.C., and connect with SR 258 for Deale or S.R. 261 for Herrington Harbour South. It’s about an hour, on a good day, from downtown or Baltimore, and about two hours if you’re driving up from Richmond.

The waterfront pool is a big attraction at Herrington Harbor North.

Marina Basics

If you are looking for a family-friendly, get-away-from-it-all weekend, you may want to head directly for Herrington Harbour South. Here, you’ll have easy access to the Bay from the comfort of its entirely protected boat basin, with 600 slips. There is an excellent restaurant, your own sandy beach and swimming pool, an inn and takeout food, beer and wine at Chesapeake Market & Deli. On the other hand, Herrington North has fixed and floating docks accommodating up to 70 feet, three lounges, a saltwater pool and jacuzzi, complimentary kayak and bike rentals, and easy proximity to classic hangouts in nearby Deale.

If you bear right coming up Rockhold Creek and take a slip at Shipwright Harbor Marina, you can find plenty to make you happy, including dingy or water-taxi access to the local favorites Skipper’s Pier Restaurant & Dock Bar, plus a saltwater pool, bikes and kayaks.

Above the Deale Road Bridge, which has a vertical clearance of 14 feet, you’ll find two more good options, especially if you are trailering your boat in. Harbour Cove Marina has wet and dry slips, a pool and clubhouse and it’s within walking distance to restaurants and a hardware store. Just beyond, Hidden Harbour Marina offers slips, a playground for kids, the Boathouse Bar for adults and the popular Anchored Inn. Globally famous Weaver Boats, which builds exquisite sportfishing yachts, is located just next door.

The entrance channel to Herrington Harbor South.

Staying on Land

The Inn at Herrington Harbour South is a full-service, family-friendly resort, built in the 1950s but updated with comfy rooms and suites with perks like hot tubs and full kitchens. Enjoy the seasonal waterfront pool and beach, two dining options (Ketch 22 and the take-out Chesapeake Market & Deli) and a landscaped waterfront garden that is a popular spot for weddings.

Located in Deale, the Anchored Inn at Hidden Harbour opened in 2016 and welcomes you and your pet to enjoy 16 comfy rooms, free parking and seasonal outdoor pool, plus easy access to the Boathouse bar and a few local shops.

Exploring by Water

If you are bringing a canoe or kayak, you’ll find a number of places to launch, including the beach at Herrington South and most of the marinas on Rockhold Creek. Or rent double kayaks, SUPs or paddle boats from Chesapeake Paddle Sports, which also offers guided sunset eco tours. You can easily explore Herring Bay and Rockhold Creek, which meanders peacefully above the Deale Road Bridge for about two miles, and also take a turn down adjacent Tracy’s Creek, which runs for about a mile above the S.R. 256 Bridge north of Herrington Harbour North.

Fishing is big business in Deale, with more than 40 charters coming in and out. Last Hurrah, Lucky Strike and Ebb Tide are three that we like, but there are plenty more.

Exploring by Land

Deale doesn’t have a proper downtown; it’s more of a collection of businesses and homes that run along Rockhold Creek, including the adjacent community of Tracey’s Landing. Look for treasures at Second Wind Consignments, A Vintage Deale and Blue Heron Boutique. Hit West Marine for supplies or get prepped for fishing at Tri-State Marine Tackle & Gifts.

Bar Crawling

Nightlife done right at Herrington Harbor North

This port is home to four well-loved dock bars, accessible by dinghy, kayak, car or bike—whatever you have. Skipper’s Pier Restaurant & Dock Bar is the first thing you’ll find on entering Rockhold Creek, on the north end of the bay. Owners Dave and Jessica Rosage set Skipper’s apart from your average dock-and-dine facility with regional musts plus unexpected dishes like rockfish Reuben and seafood pot pie. If you love dive bars (and we do!), you’ll love the famous Happy Harbor restaurant, which has been serving local watermen, residents and visitors since 1933. You can get everything here from cold beer and fried pickles and to steamed clams and cheeseburgers, best enjoyed on the deck as you watch the charter boats come and go. Dockside Restaurant and Bar at Herrington North has a big covered patio and waiting area on the side lawn, while the Boat House at Anchored Inn serves up crushes, beer and wine from their boat-turned-bar, set under a weathered wooden boat house. Happy Harbor is open from 8 a.m. til midnight (2 a.m. Saturdays); the rest close up earlier.

Want to take to bring the bar with you? Bring five of your friends along for a two-hour trek on Cruisin’ Tikis. These round floating tiki bars provide a captain, bamboo bar and thatched-roof shade; you bring along the bevvies, snacks and the floaty toys for when you need to jump in and cool off.


South County Café has the best breakfasts around, served until 11 a.m. daily, followed by lunch specials like wraps and sliders. Homemade treats are served all day from the onsite bakery.

Located at Herrington Harbour South, Ketch 22 is a fantastic restaurant owned by the same team that runs The Point in Arnold (voted Best Crab House in CBM’s 2022 Best of the Bay). Their inspired menu of Chesapeake cuisine includes crab soups and cakes, tacos, fish ’n’ chips and steak frites.