Where to Stay Along the Great Chesapeake Bay Loop Pros & Cons Pros Exceptional golf Fresh, local seafood Children's program Quiet but with a host of waterfront activities, Oxford was once an international shipping powerhouse. It is a 400-acre native garden and preserve inclusive with a water-view to set picnic. Nicknamed the Jewel of the Chesapeake Bay," North Beach is hopping with things to do, like the free summer concerts, beach-side movies and the Friday Night Farmers Market. The quintessential town is an ideal Chesapeake destination for families, home to a world-class museum and charming main street with art galleries, luxury hotels and historic inns. Local tip: Tie up and crack crabs at the Watermans Crab House. Local tip: St. Michaels looks even prettier from the Miles River. For seafood aficionados traveling to the Chesepeake Bay, a visit to Urbanna should be on the docket. At the lighthouse, you're able to see amazing views of the Chesapeake Bay, and while on the fishing pier, feel free to watch the sunrise and watch birds in the fresh air. All around the bay, towns from the colonial era that were once tobacco ports, fishing centers, or railroad and ferry hubs have transformed into beautiful bayfront communities. All maps, graphics, flags, photos and original descriptions 2023 worldatlas.com. 6 Md. Communities Make Magazine's List for Best Bay Small Towns Oxford has resisted the development and glitz of neighboring Easton and St. Michaels, instead exuding a quiet charm. Calvert Cliffs State Park is one of the best things to do in the Chesapeake Bay area and is a true gem on Maryland's Eastern Shore. 10 Fun Things to Do in Chesapeake Bay from $10 | Expedia Take a bike with you to sight-see, rent a golf cart or go bird-watching. Baltimore's crown jewel is best experienced from the water, via charter boat or water taxi. In recent years Cambridge has been rated one of the most livable small towns in America due in part to its revitalized downtown area that bustles with shops, restaurants, festivals, and farmers markets. It is considered to have the largest shipwreck fleet in the Western Hemisphere, with more than 200 hulls of ships resting here. Come and engage with Marylands Chesapeake Bay, the largest estuary in the United States and a place of serene beauty. Take a Tour of Maryland's Lighthouses | VisitMaryland.org If we are up and awake we will answer the phone or email. While a USDA Natural Amenities Scale gives Annapolis and the rest of the Chesapeake Bay region average rankings on scenery and climate. Today, Chestertown is home to Washington College, a number or restaurants and historic attractions. There are tons of unique stores, and antique shopping for new home decor, memorabilia, and souvenirs for others. Chesapeake Bay region best place to live? Outside Mag: Yup. Fed Gov't Sail on the skipjack Nathan of Dorchester, walk in the footsteps of Harriet Tubman, and enjoy the hip culinary and art scene of downtown. Pell Gardens is one of the prettiest town parks in the Chesapeake Bay region. Situated along the Chesapeake Bay on Maryland's Eastern Shore, Oxford has a full-time population of fewer than 1,000. Real Estate & Homes For Sale - 9475 Homes For Sale | Zillow Chesapeake Bay Media All rights reserved. Walking and paddling trails give visitors a chance to explore this unique ecosystem. There is a rich and interesting history at Fort Monore in Hampton VA. Historic points of interest, amazing architecture and a scenic waterfront location make Portsmouth a top getaway destination. It is a beautiful, small watermen's community where Chesapeake Bay skipjacks and workboats abound, harvesting oysters, crabs and rockfish. North Beach, Maryland, has a half-mile long boardwalk and seven blocks of waterfront. The cultured will love Bay-inspired works by nationally renowned artists, along with catching a screening at the old-school Roseland Theatre. While small in size, Cape Charles is renowned for the number of well-preserved Victorian-era houses in town, vestiges of its past as an important railroad and ferry terminal. Cambridge, Maryland is a picture-postcard story of a historic coastal town with brick-paved streets, museums, parks, and of course a charming lighthouse on the water. Home to waterfront bars and open-air crab houses, Deale is perfect for anyone looking to hit the open water for the day and then enjoy a good meal afterwards. Chesapeake is the largest estuary in the nation where waters from inland rivers meet with the Atlantic Ocean and where vacationers have met with relaxation and fun for years. Onancock is a real charmer, dubbed the gem of the Eastern shore by Captain John Smith in the 1600s. John Smith Chesapeake National Historic Trail. Stroll the Promenade boardwalk next to the lighthouse for a lovely view of the water. 11 Charming Small Towns You Need to Explore On Your Next Chesapeake Bay The handsome Victorians in this town at the tip of the Delmarva Peninsula are a reminder of its railroading heyday. We Looked for Freakness. Here are a dozen places to check out. Did you know Red Beard Sailing offers free shipping on all boats to the lower 48 states? Chesapeake Bay, which is the largestestuaryin theUnited States, is bordered by the mid-Atlantic states ofMaryland(to the north, east, and west) andVirginia(to the south). There is a parade, exhibits, and other fun discoveries of heritage and modern life on the bay. Norman Gross recreates the Bay boats of his childhood. Settlement Reached in Suit Over Pennsylvania Pollution - Chesapeake Bay Discover the 8 most charming towns along the Chesapeake Bay. Sittin on the dock of the Bay watching the tide roll away Any number of people who love the Chesapeake dream of making Otis Reddings words their reality when retirement comes knocking. Do you want to get away from it all, or to it all? Though known for its oyster festival every November, this former tobacco portwith a boating scene along Urbanna Creek and 18th-century buildingsis far prettier when the weathers warmer and an extra 50,000 to 75,000 people arent around. For those looking to cruise the open waters, Kent Island offers unique access to the Eastern Bay, Chester River, and the heart of the Chesapeake Bay itself. Sometimes referred to as the Sailing Capital of the U.S., Annapolis is home to various boat shows, the Naval Academy, and the National Sailing Hall of Fame. Truly, when it comes to seeing the charm and inviting hospitality of these towns along the estuary, the only question should be: where to start? What began as another sleepy town on the shores of the Chesapeake at its founding has become a boaters paradise. St. Michael's bustling downtown area is chockfull with varied boutiques to stock-up on gifts and great home-finds like artisanal olive oil and antiques. Apparently, something about the town and the bay nearby inspires artistic expression and it is easy to see why. Onancock's small-town appeal envelops world-class amenities, a thriving arts scene, museums, and restaurants for any taste and style. Located on the western shore of the bay, Galesville is a small town that sits along the West River. Note: Please check local Covid-19 updates to make sure places are open before you go. PHOTOS: The Most Expensive Homes Sold in Washington in May. Copyright 2023 Visit Maryland, Maryland Office of Tourism Development. Oxford was founded in 1683 as one of Maryland . There's so much to sight and experience in the charming village of Southern Maryland, starting with a great boardwalk. Flickr / Chesapeake Bay Program. Located along the Chester River, Chestertown was once one of the six Royal Ports of Entry and considered Maryland's second leading port. A day of cruising in Rock Hall will give you access to beautiful scenery and plenty of open water to explore. Independently owned, Red Beard Sailing is your one-stop-shop for mini catamaran, small catamaran boats, inflatable dinghies, sailing accessories, & more. Choose a destination from the list or map below and be one your way! One can start experiencing all the scenic town has to offer by waking up with a view at one of the charming bed and breakfasts lining the waterfront. Whether you approach them by boat or by car, waterfront bars are the best place to spend a summer afternoon watching the water (or a game on TV). Someplace with great seafood restaurants and a museum that puts you in touch with Chesapeake traditions? Established in 1649 and made state capital in 1694, Annapolis sits at the mouth of the Severn River and is fewer than 35 miles from bothBaltimoreandWashington, D.C. Home of one the East Coasts premier sailing schools, Irvington is the perfect place to learn the ropes. With a population under 40,000 and a bayfront location,Annapolisis one of the smallest but most beautiful state capitals in America. Sandy Point State Park. Best Historic Water Trail: Capt. Point Lookout State Park. The Chesapeake Bay is the one famous one and the only main direct way to the Atlantic beaches of Delaware, Maryland and Virginia. If you want to retire in Chesapeake Bay country, the decision to make is where, exactly. Outside magazine ranks Annapolis the #13 best place to live in America. Oxford was founded in 1683 as one of Marylands first two ports (along with Annapolis) and maintains a restored colonial-era customs house and other historic sites. Jun 27, 2016 The sun sets over Chesapeake Bay With its rich maritime history, picture-postcard towns and endless coves, creeks and anchorages, there are few places on Earth that are as easy and fantastic to sail as the Chesapeake Bay. Home port of the schooner Sultana and home to a thriving arts community, this beautiful historic college town is just up the Chester River on the Eastern Shore. Charter boats abound for fishing trips and the Calvert Maritime Museum is home to river otters, Drum Point Lighthouse, tour boats, a paleontology gallery and lab, and more. Kent Island. This Maryland state park is picture perfect for a day in the sand and water. With easy access to fishing and crabbing destinations, the Wye River is a favorite cruising destination for many. The historic area sits just south of the Chesapeake & Delaware Canal, a 14-mile canal that dates back to 1829. Virginia Is About to Require Age Verification to View Porn. Today, you can spot wildlife taking shelter in the Ghost Fleet of Mallows Bay, with Ospreys and Bald Eagles nesting nearby, and you can also go kayaking among the wrecks. North Beach. Limited public tours are available throughout the year, departing by boat from Annapolis. (410) 705-5026Please feel free to contact us, day or night. The Maryland capital might be the capital of Chesapeake towns, with the historic city located on the Severn River, a stone's throw from the Bay Bridge, and sailboats always in sight. The Lafayette Trail, a three-mile loop, will give you a nice overview of the historic district, parks, and views of the Susquehanna River and Chesapeake Bay and can be enjoyed with pets.