Best Marina for Entertainment

FIRST PLACE WINNER

The Shanty Beach Bar at Tolchester Marina

Chestertown, MD

When it comes to an ideal summer getaway, boaters yearn for a beachside retreat laden with tempting summer spirits, mouthwatering munchies and top-notch live entertainment. This year’s winner of the Best Entertainment category, Shanty Beach Bar at Tolchester Marina, offers all that and more. Situated in a quaint Chesapeake Bay town along Maryland’s Eastern Shore, the marina is conveniently located at Buoy 21, just 20 miles north of the Chesapeake Bay Bridge and 30 miles south of the C&D Canal. 

Shanty owner Cathy Bramble says some of their transients “have been coming to Tolchester for 30 years or more, and they consider themselves part of the family.” Making strangers feel welcome is not new to the area. During the late 19th and early 20th centuries, millions of Baltimoreans traveled by steamboat to the amusement park at Tolchester Beach Resort to ride the carousel, picnic in the shaded pavilions and wade along the sandy beach. 

Today, savvy boaters seeking a laid-back weekend escape travel from all around the bay to dock in a protected slip at full-service Tolchester Marina and head straight for the big red umbrellas at The Shanty Beach Bar for a snack and a cool beverage. Visitors can still splash around on that same large, unspoiled sandy beach. 

The Shanty has a friendly, hang-loose atmosphere and is staffed with the same friendly folks from the previous season, as is most of the entire Tolchester facility. The familiar-faced bartender remembers your favorite drink from the innocent-seeming Mudslides which flow down way too easily to the delightfully delicious Orange Crushes. If you just want a simple cold beer, they will probably remember that too. 

The sounds of live music ride the Chesapeake Bay breeze on Fridays and Saturdays throughout the summer. It is not uncommon for almost a hundred boats to drop anchor off the Tolchester Beach to hear the live music. Touring regional and local acts take to the bandstand to offer a variety of musical genres, with southern and classic rock bands among the many favorites. “There’s something for everyone in an atmosphere that all can enjoy,” says Bramble. 

In addition to the afternoon and evening jam sessions, there’s a patio on the hill perfect for viewing passing ships and taking in the spectacular sunsets rivaling those of Key West. The marina boasts over 250 slips with fixed, floating and covered options. Boaters can enjoy amenities from newly renovated private bathhouses, a fitness center, fuel dock, picnic area and waterfront saltwater pool. Tolchester’s seasonal Channel Restaurant, open for breakfast, lunch and dinner, has earned a long-standing local reputation for having the best crab cakes on the Bay!

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HONORABLE MENTION 

Shelter Cove Harbour & Marina 

Hilton Head Island, SC 

Trailing closely behind Tolchester, our honorable mention for this category is Shelter Cove Harbour & Marina, located just off the ICW in the heart of Hilton Head. Neighboring the Palmetto Dunes oceanfront resort, this is a hot spot for dining, shopping and entertainment, as well as local arts, family activities, festivals and live music from the island’s favorite bands. Catch crowd pleasers such as Deas-Guyz, performing an entertaining mix of old Motown, R&B, pop, reggae and various genres of dance beats. 

Pet-friendly outdoor concert series are a lively attraction at this resort destination. Dance the night away to live music on select Thursdays during the spring and fall, held at two participating Shelter Cove Harbour & Marina restaurants. 

Shelter Cove also hosts HarbourFest, a weekly Tuesday-night summer celebration featuring live music, family-friendly entertainment and fireworks sure to elicit the familiar appreciative “oohhs” and aahhhs” from spectators.