Fabulous Fall Boating on the Chesapeake Bay

By September 30, 2022October 3rd, 2022Dock, Explore

You’ll fall in love with fall again, on the Chesapeake Bay. In the Bay, the weather is still warm during the day and refreshingly mild at night, and the water is teeming with fish. Boat traffic, and the pace in general, calms down. For boaters, it’s nothing short of glorious!

All along the waterways of the Chesapeake, there is still a boatload of activities for every member of your crew to enjoy. Take in live concerts, seafood festivals, fishing festivals, and restaurants and bars with breathtaking sunset views. You can bet your first mate that you won’t run out of fun and entertaining things to do, or spectacular scenery. For that matter, check out a complete and up-to-the-minute list of fall activities for Maryland and D.C. here.

With so much to do in the Chesapeake Bay, the gang at Snag-A-slip has put together their favorite stops, eats, and marinas. We know you won’t be disappointed.

Eat your way around the Chesapeake Bay


When given a choice, a boater will always choose to cruise right up to a dock, hop out of their boat, and into a bar or restaurant. What they enjoy most while eating are beautiful water views, and, of course, views of their boat! When it comes to docking and dining, you can’t go wrong with the Dock House in Kent Narrows, Maryland. It features a variety of coastal cuisine including fresh seafood, fresh ingredients, and seasonal produce, locally and sustainably sourced. It serves up hands-down favorites year-round. Of course, the panoramic views of the Kent Narrows from their wrap-around deck make this an easy choice.

If you want fresh Maryland crabs steamed to perfection and jerk chicken that will make your mouth water, The Jetty is the place to dock. Also on the Kent Narrows in Grasonville, Maryland, it’s known for its great food and friendly faces. It’s also known for its oysters on the half shell, jumbo lump crab cakes, and fish-N-chips. Oh, it has a doggie menu too. Yes! Grilled chicken breast and a burger patty will be served up for your four-legged crew member. 

The Red Eye’s Dock Bar is a classic belly-up-to-the-bar local’s favorite. But on top of the impressive beer selection and frozen concoctions, the menu has delights like Mexican street corn, garbage can nachos, and crabby fries. This iconic waterfront dock bar is on the Kent Narrows in Grasonville, Maryland. In addition to waterfront views from just about every seat, it books great live bands to get you moving and shaking.

Cruise on up to Kent Island


The largest island in the Chesapeake Bay, filled with history, is picturesque Kent Island. Just barely separated from the mainland by a narrow channel known as Kent Narrows, it is a popular boating destination. You can stretch your legs at one of the many natural areas or enjoy a classic Chesapeake Bay meal at one of the many restaurants – five-star to no-shoes-required.  There are also lots of hotels on the island if you want to take a break from your beloved boat.

While there, you’ll revel in the impressive list of distilleries and wineries, outdoor activities, historic places, resorts, and restaurants. 

And if you didn’t know, Kent Island has very deep roots in Maryland history. Founded in 1631, Kent Fort is the third oldest English settlement in the country – after Jamestown and Plymouth. Before the iconic Chesapeake Bay Bridge opened in 1952, the area served as a hub for steamboat travel.

Annapolis is a must see


Annapolis, Maryland has earned the name of Sailing Capital of the U.S. for good reason. It has everything a boater could want and need. Spectacular water and shoreline, great fishing, fascinating wildlife, every watersport imaginable, and a city that never sleeps. From island hopping and boat shows to entertainment, shopping, and a culinary cornucopia, Annapolis is first-rate as far as boaters are concerned.

But when it comes to doing what boaters like best, there are endless cruising activities. A pastime totally unique to Annapolis is boat spotting on Ego Alley, off Dock Street in the city. The name gives it away, but we’ll explain it anyway. Ego Alley is a well-known waterway where some of the most luxurious, off-the-charts boats line up. You can view these beauties from your own boat and marvel at the specimens on display. You’ll no doubt find many other boaters drooling over these behemoths. 

In the northern end of the bay, near Baltimore, sits Hart Miller Island, a hugely popular spot for boating enthusiasts. It’s the ideal place to moor your boat and romp in, or lay near, the fantastic beaches.  The island is a family-friendly state park and offers moorings for boats and camping facilities. There’s not much on the island but glorious nature, so bring plenty of sunscreen, water, eats, and refreshments. And, you’ll need to take your litter home with you!

Where to dock


Bay Bridge Marina

Bay Bridge Marina in Stevensville, Maryland, is conveniently located at the base of the Chesapeake Bay on Kent Island. A great location for boaters on the Bay, it’s within minutes of Annapolis and Baltimore. The marina offers resort-style amenities and top-notch marina services, not to mention friendly staff. Guests can enjoy the pool and poolside Tiki Bar, the fitness center, pristine restroom and showering facilities, a captain’s lounge, a fully stocked Ship Store, and much more. The marina fuel dock is open year-round and offers complimentary pump-out service.

Kentmorr Marina

Kentmorr Marina in Stevensville, Maryland, is a sport fisherman’s paradise. For that matter, it has over 20 Charter Boat Captains on-site during the fishing season. Guests have easy access to prime fishing spots directly outside the channel, saving time and fuel. This full-service marina is located next to the Bay Bridge allowing quick access to the Middle Bay, Annapolis, Eastern Bay, and many Kent Island destinations. It has something for all your maritime needs including gas, diesel, pump-out service, and ice. It is also staffed with knowledgeable management personnel and service technicians who can provide all you require for year-round marine service and maintenance. Guests also enjoy the on-site restaurant, Caribbean-style tiki bar, beach access, heated bathrooms, shower facilities, and complimentary WiFi.

Wells Cove Marina

Wells Cove Marina in Grasonville, Maryland, is centrally located and serves as one of the area’s great launching pads for day trips to wonderful locations such as Rock Hall, Baltimore, quaint St. Michael’s and historic Annapolis. The marina has a pool for relaxing and sunbathing, and is within walking distance of popular restaurants and bars, including The Jetty and The Big Owl Tiki Bar. There are lots of outdoor activities nearby and many regularly scheduled events. Despite being in the center of things, the marina maintains a romantic, quiet vibe for couples and families.

Port Annapolis Marina

Port Annapolis Marina in Annapolis, Maryland, offers a  resort-like setting that will appeal to the entire crew. With plenty of on-site amenities, including a pool, playground, sundeck, restaurant, and more, you won’t want for anything. You can explore the local area, and convenient downtown Annapolis and Eastport – the marina even runs shuttles during the Summer! If it’s social activities you desire, the marina hosts a long list of summer events and regular gatherings, such as Game Nights in the lounge.

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Jo Montgomery

Author Jo Montgomery

Jo is a lifelong boat lover and writer. She learned the ropes of boating on her family’s 36’ Carver at the Jersey (joy-see) shore. With over 30 years of writing under her belt, she delights in seeking out, and sharing, the things most important to fellow boating enthusiasts. Jo now lives in Connecticut, near the water she adores, with her husband, two children and large, hairy dog. She is over the moon to be part of the Snag-A-Slip crew!

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