Other not-to-be-missed sites are the world-renowned Havre de Grace Decoy Museum and the downtown shopping district. Someplace with great seafood restaurants and a museum that puts you in touch with Chesapeake traditions? Story and photos by Charlie Youngmann. We Looked for Freakness. Cambridge in Dorchester County. It is now a hot spot for pleasure boating and home of the West River Sailing Club and Hartge Yacht Harbor. Explore 8 ideal destinations for a 3-day weekend on the Chesapeake Bay. Address: 1100 E College Pkwy, Annapolis, MD 21409. just as it retains its original cobblestone streets and quaint architecture. Mallows Bay is a small bay on the Potomac River, with public boat access from Charles County. Sitting at the mouth of the Susquehanna River and the head of the Chesapeake, Havre de Grace is uniquely positioned to several state parks and scenic views including Elk Neck State Park and Susquehanna State Park. Local tip: Tie up and crack crabs at the Watermans Crab House. The AARP Livability Index, for example, examines facts and figures related to an individual communitys housing, neighborhoods, transportation options, environment, health, engagement, and opportunity. (410) 705-5026Please feel free to contact us, day or night. Easton Maryland, named one of the Best Small Towns in America, is nestled on the eastern shore of beautiful Chesapeake Bay. Local tip: Settle in with a New York Times and an espresso at the Local (4337 Irvington Rd. The towns historic district is full of brickwork, with many of the homes having been built in the 1800s. Ride a passenger-only ferry to the home of the famous Smith Island Cake (the state dessert) and listen to the distinctive Elizabethan accents, remnants of the original English colonial settlers. The rich cultural spirit extends into the varied cuisine options to choose, from pub food to fine Italian dining, housed in quaint little restaurants. Or, rent a kayak and travel up the Chester for a change of pace. We pulled in accolades from a few other sources, and finally added our own intimate knowledge of the region to create a list of retirement bright spots, while providing alternatives for each pick that are either cheaper or geographically different. Bay Living Best Places to Retire by the Bay By Chris / March 1, 2021 Looking to settle down on the Bay? If you want to retire in Chesapeake Bay country, the decision to make is where, exactly. We Found Preakness Instead. Shop and dine along the towns Main Street or charter a boat for an unforgettable Bay tour. And last but not least, what can you afford? It is considered to have the largest shipwreck fleet in the Western Hemisphere, with more than 200 hulls of ships resting here. A quintessential piece of Americana, this town of roughly 400 was called one of the 20 best places to live on the coast by Coastal Living Magazine in 2020 and it is easy to see why. Come in July to the Taste of Cambridge Crab Cook-Off and Festival for some of the best crabs youll ever eat and take a ride on the skipjack Nathan of Dorchester. White picket fences and billowing sails in the Rappahannock river abound in Irvington. Nestled along the Miles River, this chic historic waterfront town is home to museums and boutiques, gourmet restaurants and crab houses. Watch sailboat racing at the annual Turkey Shoot Regatta from the shore for an exhilarating evening. 2. 01 of 07 Best Overall: Tides Inn Tides Inn See Rates on Tripadvisor.com Why We Chose It This hotel, set on a striking waterfront property, offers all the Chesapeake Bay area outdoor activities travelers (and locals) could ever wantand the rooms are exquisite, to boot. Roadtrip-worthy towns to visit in the Chesapeake Bay region. Druid of the Chesapeake Honored with Award, Bay Paddle Returns to Raise Money for the Bay; Plans Rockin After Party in Rock Hall, Leave Stress Behind in Queen Annes County. Visitors to these charming towns get to taste the past, with colonial architecture and historic sites, along with modern dining, shopping, and entertainment options. Smith's is the National Park Service's only all-water National Historic Trail. Chesapeake Bay (Maryland) - All You Need to Know BEFORE You Go 1. 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. The Chesapeake Bay Loop - A Pet Friendly Road Trip Local tip: Start the day with the famous French toast at Cape Charles Coffee House (241 Mason Ave.; 757-331-1880), in a 1910 former bank with Art Deco chandeliers. The charming town with a ring of romance in its name, boasts big personality. With breathtaking views of the Patuxent River and sunsets, this working waterfront community is a perfect mix of traditional and contemporary, served at a laid-back pace. Chesapeake City is also built on one of the largest working commercial canals in the world. Fells Point is a hip neighborhood of bars, restaurants and row homes that hosts visiting ships and markets in Broadway Square. Best Places to Retire by the Bay - Chesapeake Bay Magazine 9 Places Where You Can View The Chesapeake Bay Bridge In Maryland Most of the homes have been restored and colorfully painted, making for a pleasant stroll for historic house gazing. Numerous organizations and websites crunch the data on communities to rank or grade them. If you bring your own vessel, try to time it when one of the concerts is performing at the MECU Pavilion(formerly Pier Six Pavilion) on the harborboats idle outside to catch the performances. Add in the Wye Island Natural Resource Management Area, and you have a perfect destination for cruising and exploring the outdoors. Located on Maryland's Eastern Shore, St. Michael's, Maryland has plenty to offer despite being home to a little over 1,000 people. Just a short drive from Baltimore, where the Susquehanna meets the Chesapeake, Havre de Grace is full of history, shopping and things to do. Easton in Talbot County. Once home to canneries and seafood-packing houses, Cambridge now claims an up-and-coming main street with restaurants and galleries, not to mention the riverfront Hyatt Regency Chesapeake Bay, a good base from which to explore Blackwater National Wildlife Refuge, about ten miles south. These eight towns along the Chesapeake Bay offer perfect sea-scape that charms from the first glance and pulls one in for life-long memories. With access to a number of marinas, the Inner Harbor is a great launch point for day cruising. While scores technically range from 0-100, anything above 50 is good. Coastal Living also deemed Virginia's bayfront hamlets of Cape Charles, Onancock, Urbanna and Yorktown among the best small towns on the Chesapeake Bay. The Inn at Perry Cabin by Belmond, St. Michael's. Sagamore Pendry Hotel, Fells Point Waterfront in Baltimore. Local tip:Evergrain Bread Company(201203 High St.; 410-778-3333) has some of the flakiest croissants this side of the Seine. Urbanna also hosts a monthly farmers market and an annual arts festival. Tilghman Island, atraditional waterman's village on the Eastern Shore, is accessible via a drawbridge. The environmentally sensitive setting of wildlife, waterfront, and canopied woodland, also gives access to public parks. Home to Washington College, this towns restored 18th- and 19th-century rowhouses and cobblestone streets abut the picturesque Chester River. Steeped in the history, culture, and ecology of the beautiful Chesapeake Bay, our Storytellers are trained and dedicated to connecting you more deeply to this true global treasure. Its been called the St. Michaels of Virginias Eastern Shore for its urbane restaurants, inns, and galleries, but this port town still has plenty of down-home charm. Oxford has resisted the development and glitz of neighboring Easton and St. Michaels, instead exuding a quiet charm. They are owned by a bank or a lender who took ownership through foreclosure proceedings. Best Beaches in Maryland for 2023. World-class museums, thriving arts and culture districts, history, nightlife, music and more make Baltimore the urban jewel of the Chesapeake Bay. One must visit the bay's oldest lighthouse with amazing views of the Chesapeake Bay, stroll the perfect marina, and watch the sunset from the fishing pier. Located at the mouth of the Chester River, this town of under 1,500 boasts over 10 marinas, a yacht club and world-class sailing. This town boasts more boats than folks, and is an exemplary way to destress and decompress into the island groove (at least when the oyster festival is not on). Food boats ply the water in summer as families enjoy the island beaches, or cook out on the mainland at Rocky Point Beach and Park. The best time to hunt is after a big storm, when new specimens are revealed. 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. Onancock was namedThe Coolest Town in the South for delivering a relaxing experience within authentic Eastern Shore atmosphere. Explore Used Boats. Best Places to Live in Chesapeake, Virginia - Sperling's BestPlaces Starting at the still-in-use 1779 Maryland State House, Annapolis visitors can walk down a gentle hill through colonial-era streets full of shops, galleries, pubs, and restaurants to reach the stunning waterfront. Boat rentals and public water access let you experience it for yourself. For travelers in search of the perfect picture, Cape Charles is a photographers paradise. 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. More Information. Baltimore, Maryland is a historical city, being home to both the battle that inspired the Star Spangled Banner and renowned poet Edgar Allen Wright. Chesapeake Bay Areas St. Michaels, Maryland St. Michaels is one of a cluster of Maryland's scenic harbor towns including nearby Easton and Oxford. Enjoy prime bay-to-table dining and pedal about this quaint shoreline town in Virginias river realm. Home of one the East Coasts premier sailing schools, Irvington is the perfect place to learn the ropes. A version of this article appears in our July 2016 issue of Washingtonian. TRENDING: C&D Canal Bike Trail: What You Need to Know on the. Oh, and those amazing Chesapeake Bay vistas and cool, waterfront breezes are a must. 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. 15 Best Things to Do in the Chesapeake Bay Area You Must Visit Best Places to Retire by the Bay By Chris / March 1, 2021 Photo: Hope and Glory Inn Irvington, Va. Population 400 Yours Truly Photography A small yet sophisticated charmer on Virginia's bucolic Northern Neck, Irvington's remoteness may appeal to those no longer commuting. 10 Best Chesapeake Bay Towns You Must Visit - Southern Trippers Guess Which State Is Tops for Searching for Information About VPNs? And of course a lighthouse or a skipjack. 18 Charming Waterfront Towns In Maryland - Only In Your State Try the innovative cuisine like fruit pizza at the famed Dockside Cafe or pick up a pair of root-beer floats at Durdings Store. Destinations There is a rich and interesting history at Fort Monore in Hampton VA. The Maryland blue crab is renowned for its delicious, fatty meat and one would be hard pressed to find a restaurant in town where this crustacean was not on the menu. The handsome Victorians in this town at the tip of the Delmarva Peninsula are a reminder of its railroading heyday. There, fresh Virginia apples are distilled into seasonal cider varieties like Habanero Mango and Watermelon Rosemary. Want to try sailing? With a maritime and colonial heritage, youll feel the history as you walk along the beautiful brick roads and view the architecture that has been preserved from the towns beginnings. For dining, there's the Bizzottos Gallery-Cafe serving dishes with an Argentinian-Italian flair, or the Irish-scene at the Blarney Stone Pub. There's so much to sight and experience in the charming village of Southern Maryland, starting with a great boardwalk. All maps, graphics, flags, photos and original descriptions 2023 worldatlas.com, 9 of The Friendliest Towns In Chesapeake Bay. Traipse through the Ben Cardin C&D Canal Trail to take it in at the waters edge. 9 Underrated Destinations In Michigan To Avoid Summer Crowds, These Small Towns in Florida's Emerald Coast Come Alive in Summer, 7 Most Underrated Cities In South Carolina, 9 of the Friendliest Towns in Pennsylvania. Located along the Tred Avon and Choptank Rivers, Oxford, Maryland is home to the Oxford-Bellevue Ferry, the Tred Avon Yacht Club, and the Oxford Museum. ; 804-438-9356), a place where locals actually do congregate. With the land changing due to erosion, storms, and rising seawaters, you should visit it while you still can. To explore, start on Main Street and work towards the Watermans Museum for a dive into Rock Hall history. The promenade of the town's historic downtown area is great for an atmospheric and relaxing evening-full of great shopping and dining. Throughout this Historic District, Annapolis maintains many homes, buildings, and markers dedicated to preserving the history of African Americans in the area. Covering over 4,000 square miles, there is plenty to explore. 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. The Urbanna Seafood & Raw Bar does offer half shell oysters year-round, however, but this town has so much more in store than shellfish. Travel Onancock Creek by kayak up to a local winery before visiting the island of Tangier from the towns port. Ships and tugs traveling the Chesapeake and Delaware Canal pass through the center of the historic city on their way to and from Baltimore, Delaware and New York. Book a tour with Captain Iris Clarke on the Selina II(410-726-9400), a sleek cat-boat from the Gatsby era. Where to Stay Along the Great Chesapeake Bay Loop It is the first town drivers reach after crossing northward over the Chesapeake Bay Bridge Tunnel, which opened in 1964 and spans over 17 miles across the mouth of Chesapeake Bay. Virginia Is About to Require Age Verification to View Porn. Only 500 people or so call Irvington home, but its upscale boutiques and places to stay lend this idyllic burg a sophisticated feel. 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. Chincoteague Island, Virginia View of the Chincoteague Bay Waterfront, in Chincoteague Island, Virginia This tiny fishing town is the nation-renowned destination for most-charming wildlife sightings. St. Michaels in Talbot County. From fishing and national parks to delicious food like crabs and oysters, the Chesapeake Bay has a lot to offer. Try Pier 450 in Ridge, then head up the Bay to Abners Crab House on Chesapeake Beach and Kentmorr Restaurant in Stevensville. Ocean City Flickr / Bernt Rostad The town with a big name comes with a whole vacation-worth of activities to charm all of one's senses on a getaway from the real city. Pro tip: book a table outside for an unbeatable view of the sunset. Ha. Take a Tour of Maryland's Lighthouses | VisitMaryland.org 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? 213 will keep you along the less-hectic Eastern Shore and expose you to a number of bay towns (Chesapeake City, Chestertown, Queenstown to name a few) and tributary rivers along a scenic route before . 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. Its glimmering surface is a jewel in the Mid-Atlantic which is known for its world-class fishing and astounding natural beauty. Limited public tours are available throughout the year, departing by boat from Annapolis. A day of cruising in Rock Hall will give you access to beautiful scenery and plenty of open water to explore. 9 of The Friendliest Towns In Chesapeake Bay - WorldAtlas Chesapeake Bay Media All rights reserved. Shops and restaurants line the main drag, Mason Avenue, which ends at one of the nicer beaches on the bay. Discover the 8 most charming towns along the Chesapeake Bay. From the soaring statehouse dome topped with a lightning rod made by Benjamin Franklin, on down the old bricked streets and past mansions to the continuous boat parade in Ego Alley, visiting Annapolis is a capital idea. Red Beard Sailing is a premier distributor for XCAT, MiniCat, ROWonAIR, Happy Cat, Grabner, and Takacat. Historic Towns of the Chesapeake Bay | ChesapeakeLiving.com Quiet but with a host of waterfront activities, Oxford was once an international shipping powerhouse. The Scoop on the Beach at North Beach. Recreational crabbing is good this week in all regions of the Bay. Havre de Grace, Maryland, is an amazing city that has the perfect marina to dock your boat, as well as a fishing pier and lighthouse. Here are a dozen places to check out. Take a strollwith views of the Tred Avon Riveror a jaunt aboard the Oxford-Bellevue Ferry, operating since 1683. Breathe in her slightly salty air; taste the flavors of her fresh seafood bounty and farms that line her shores; enjoy her waterfront towns; talk to the locals, many of whom still have the accents of their ancestors who settled the area over 300 years ago; and feel the freedom of escaping land and being on her waters. Enjoy birdwatching, fishing and kayaking on an island with a reputation for top-notch hospitality. 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. We'll help you live your best #DCLIFE every day, The Ultimate Guide to Summer Getaways and Adventures Near DC, How to Plan the Perfect Trip to Fallingwater. One of the big advantages of owning an inflatable boat is the ability to travel where you want, whenever you want, to enjoy a day of sailing. The town with a wistful name and tiny population of some 1,500 residents is beloved for budget travels with lots to see and experience. If you have more time to visit, check out these other towns along the lower half of the Chesapeake Bay: Chesapeake BeachSt. Workboats were once a common sight in Annapolis. The thriving seaport of the past boasts a lively marina with a historic cat-boat Selina II ready to depart on a scenic cruise around the bay. Following a stroll-along the unique storefronts, the C&D Canal Museum awaits with a story about the canal from birth to its present-day role. After spending a few hours walking the quaint downtown, visitors can take a trip across the Tred Avon River to Bellevue (and enjoy the picturesque views) on the Oxford-Bellevue Ferry, in operation in various forms since 1683. The Cross Island and South Island trails provide plenty of outdoor activities across the island. All rights reserved. Nature lovers will fawn over the Patapsco-McKeldin Loop in Patapsco Valley State Park. Virginia's Chesapeake Bay Region - Virginia is for Lovers Best College Towns In Chesapeake Bay. Come and engage with Marylands Chesapeake Bay, the largest estuary in the United States and a place of serene beauty. Following a shopping spree, the restaurants galore awaits with trendy tapas bars and casual waterfront dining such as the amazing seafood joint with over 30 beers on tap. Bring the family and enjoy the view. 8 Most Charming Towns Along The Chesapeake Bay - WorldAtlas Lastly, be sure to taste the oysters, crabs and fish which were crucial to the towns prosperity at its founding and are still an integral part of Cambridges lifeblood today. 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. The Mahoney family is keeping the tradition alive. If we are up and awake we will answer the phone or email. Before leaving, try Evergrain Bread Company for some delectable, mouth-watering croissants. When General Lafayette visited the small hamlet where the mouth of the Susquehanna River meets the Chesapeake Bay, it reminded him of the French harbor Havre de Grace meaning Harbor of Grace.. Serving as the hub for Kent County's maritime industry, Rock Hall is home to the Rock Hall Yacht Club, over a dozen marinas, various charters, boat rentals, and more! 5. Whether youre looking to explore the Chesapeake with a day fishing, paddling, or sailing, our Chesapeake Bay Storytellers can open a new window on your experience. Sail on the skipjack Nathan of Dorchester, walk in the footsteps of Harriet Tubman, and enjoy the hip culinary and art scene of downtown. Will there be fun things to do and other retirees around to do it with? It is a beautiful, small watermen's community where Chesapeake Bay skipjacks and workboats abound, harvesting oysters, crabs and rockfish. Onancock's small-town appeal envelops world-class amenities, a thriving arts scene, museums, and restaurants for any taste and style. Stroll the Promenade boardwalk next to the lighthouse for a lovely view of the water. Best Places to Retire by the Bay | Chesapeake Bay Magazine You are in the right place. Rockhall has an unmistakeable fishing town feel. Most fun & popular experiences in Chesapeake Bay Tours & day trips See all 465 activities Night-Time Monuments Bus Tour with Optional Washington Monument 3h 4.7/5 (47) Free cancellation available $64 per adult Washington DC Hop-On Hop-Off Bus Tour 1d+ 3.8/5 (474) Free cancellation available $54 $49 per adult Foreclosures. New construction. Offering a wide range of scenic and historic sailing views, Chestertown is a perfect location for day cruising. Baltimore's crown jewel is best experienced from the water, via charter boat or water taxi. To see the natural beauty of the bay, take a trip to this refuge covering 25,000 acres of the Eastern Shore. 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. All maps, graphics, flags, photos and original descriptions 2023 worldatlas.com, 8 Most Charming Towns Along The Chesapeake Bay, 11 Most Beautiful Small Towns In Maryland, 7 Prettiest Small Towns In Virginia For A Weekend Escape, These Small Towns in Florida's Emerald Coast Come Alive in Summer, 7 Most Underrated Cities In South Carolina, 9 of the Friendliest Towns in Pennsylvania, These Small Towns in the Gulf Coast Come Alive in Summer. If you have more time to visit, check out these other towns along the upper half of the Chesapeake Bay: Rock HallChestertownKent NarrowsNorth EastChesapeake City. Flickr / Chesapeake Bay Program. That means there really isnt one question to ask yourself but rather several jumbled together. 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. . The prime location of where the Atlantic Ocean and the Chesapeake Bay has made Fort Monore a popular place to control. For seafood aficionados traveling to the Chesepeake Bay, a visit to Urbanna should be on the docket. Local tip: St. Michaels looks even prettier from the Miles River. North Beach, Maryland, has a half-mile long boardwalk and seven blocks of waterfront. Hemingway's Restaurant. Did we mention theres a beach, too? 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. The town has a variety of companies which offer aquatic tours for those who wish to see the bays traffic up close. Tucked between the Chesepeake Bay and the Atlantic Ocean, Onancock was called the Gem of the Eastern Shore'' by Captain John Smith, the famous English explorer in the 1600s. In addition to its local attractions, Oxford access to the Tred Avon and Choptank makes it a great cruising destination for sailors and boaters alike.
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