Ready for a coastal escape rich in seafood, sailing, and scenic views? Explore Chesapeake Bay! In this post, I’ll share the quiet harbors, scenic byways, and crab shacks I discovered around Chesapeake Bay—where every shoreline whispers history and every meal tastes of the sea. From quaint towns to historic lighthouses, Maryland’s Chesapeake Bay region offers fresh crab feasts, waterfront adventures, and a deep connection to American maritime history.
Best Time to Visit
The best time to visit Chesapeake Bay is from late spring through early fall (May to October). This is prime season for boating, seafood festivals, and soaking up warm bay breezes.
How to Get There
- By Car: Chesapeake Bay is accessible via U.S. Route 50 and I-95, with key destinations like Annapolis, St. Michaels, and Cambridge within 1–2 hours of Baltimore and Washington, D.C.
- By Air: Baltimore/Washington International Airport (BWI) is the closest major airport to the western shore; Salisbury Regional Airport serves the Eastern Shore.
- By Boat: Popular with boaters—many marinas and water taxis connect towns along the bay.
Where to Stay
- Inn at Perry Cabin (St. Michaels) – Luxurious waterfront resort with spa services and sailing lessons.
- Hyatt Regency Chesapeake Bay (Cambridge) – Family-friendly resort with golf, pools, and marina access.
Recommended Tours:
- Chesapeake Beach: Sunset Sailing Cruise with Snacks – Look out for marine life such as ospreys and dolphins. Price: From $123 per person.
- Chesapeake Beach: Guided Walking Tour to The Cliffs – A guided walking tour down to the Cliffs of Calvert. Price: From $41 per person.
- Chesapeake Beach: Private Sailing Cruise on a 42-Foot Yacht – From $654 per group up to 6.
Top Attractions
1. Unleash Your Inner Creative at the Academy Art Museum
Rating: ★★★★★
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Location:
Easton, MDHighlights:
If you're looking for a charming weekend arts escape, Academy Art Museum is just the place. About 1.5 hours from Baltimore, this beautifully preserved schoolhouse-turned-museum celebrates creativity through exceptional collections and cultural programming.Recommended For:
Art lovers, weekend explorers, families, and culture seekers.What I Love: ♥
A rich collection of works on paper from modern masters, community art classes, and an inspiring setting in an early 19th-century schoolhouse.- Admire rotating and permanent exhibitions that feature local, national, and international artists in a thoughtfully curated space.
- View significant works on paper, including pieces by Robert Rauschenberg, Pierre Bonnard, and Martin Puryear.
- Join in vibrant cultural programs—from visual arts classes and concerts to dance performances and lectures for all ages.
- Explore the heart of Easton while enjoying one of Maryland’s most respected art institutions.
Cost:
Admission is free; some events and classes may have a fee.Best time to visit:
Year-round—indoor exhibitions and programs run in all seasons.Local tips:
Check their calendar in advance—special events and artist talks are often the highlight of a visit.How to Get to Academy Art Museum:
From Baltimore, take US-301 N/US-50 E to Ocean Gateway (US-50 E). Follow signs into downtown Easton. The museum is just off the main square on South Street—look for the historic brick building.Address:
106 South St, Easton, MD 21601Phone: 410-822-2787
2. Wander Wild at Adkins Arboretum
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Location:
Ridgely, MDHighlights:
Need a refreshing day trip from Baltimore? Adkins Arboretum is just 1.5 hours away and offers a serene 400-acre escape inside Tuckahoe State Park. It’s a peaceful haven for nature lovers, plant enthusiasts, and anyone needing a quiet walk in the woods.Recommended For:
Garden lovers, hikers, families, photographers, and conservation-minded visitors.What I Love: ♥
Five miles of trails, over 600 native plant species, and a full lineup of educational and seasonal events make this more than just a walk in the park.- Wander through woodland and meadow paths, learning about plants native to the Chesapeake Bay region along the way.
- Engage in guided walks, lectures, and hands-on demonstrations that make the science of native gardening easy to love.
- Browse the charming gift and book shop—or bring a little nature home with native plants available for purchase.
- Attend art exhibitions and seasonal community events that blend creativity and conservation beautifully.
Cost:
Admission prices vary; check the website for details. Discounts may be available for members and groups.Best time to visit:
Spring for blooms, fall for colors, but open year-round with something special in every season.Local tips:
Bring bug spray in summer, and check the events calendar before you go—there’s often a fun surprise in store.How to Get to Adkins Arboretum:
From Baltimore, take US-301 N/US-50 E toward Easton. Follow signs for Ridgely and Tuckahoe State Park. Turn onto Eveland Road and look for the Adkins Arboretum entrance.Address:
12610 Eveland Rd, Ridgely, MD 21660Phone: 410-634-2847
3. Cruise Like a Local with American Cruise Lines
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Highlights:
If you're dreaming of exploring America’s rivers and coasts without leaving the country, American Cruise Lines is your go-to. With twelve modern small ships and riverboats, they deliver a luxurious, all-American cruise experience unlike any other.Recommended For:
Luxury travelers, river cruise fans, retirees, and cultural explorers.What I Love: ♥
New, eco-friendly ships, award-winning cuisine, elegant cabins, and thoughtfully curated entertainment and excursions—all with U.S. destinations and a domestic crew.Cost:
Pricing varies by itinerary and stateroom; all-inclusive packages typically start around $2,000–$6,000 depending on cruise length.Best time to cruise:
Spring through fall for most itineraries, though some routes are available year-round.Local tips:
Book early for seasonal routes like the Mississippi in fall or New England foliage cruises—they sell out fast.How to Book with American Cruise Lines:
Browse their website for itineraries, dates, and detailed cruise descriptions. Most cruises depart from major river or coastal cities with convenient transportation options nearby.Address:
Nationwide service – call or visit their website for specific departure portsPhone: 800-460-4518
4. Get Grounded with the American Chestnut Land Trust
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Location:
Prince Frederick, MDHighlights:
Want a peaceful nature escape just an hour from D.C.? The American Chestnut Land Trust in Calvert County protects 3,000 acres of farmland, wetlands, and hardwood forests—with miles of scenic trails to explore.Recommended For:
Hikers, mountain bikers, equestrians, nature lovers, and families.What I Love: ♥
A variety of hiking loops for all skill levels, a working community farm, guided canoe trips, and historical charm tucked into every mile.- Roam 22 miles of well-marked trails for hiking, mountain biking, and horseback riding through protected landscapes.
- Explore a southern network of four daisy-chained loops perfect for mixing and matching your route and trail length.
- Visit historic structures and interpretive trails that tell the story of the land and its legacy.
- Experience guided canoe trips or support the on-site community farm that helps sustain the local ecosystem.
Cost:
Free to visit; donations are welcome to support conservation efforts and educational programs.Best time to visit:
Spring and fall for cool weather hikes and colorful foliage; summer for canoeing and longer trail days.Local tips:
Download trail maps before visiting and bring water—the trails are peaceful but remote.How to Get to American Chestnut Land Trust:
From Washington, D.C., take MD-4 South into Calvert County. Turn onto Dares Beach Road, then left on Double Oak Road. Look for signage to the ACLT South Side Trailhead near Prince Frederick.Address:
676 Double Oak Rd, Prince Frederick, MD 20678Phone: 410-414-3400
You can reach American Chestnut Land Trust on a 2-hour weekend getaway from D.C. (44.8 miles via MD-4 S and MD-4 S).
5. Raise the Sails at Annapolis Yacht Club
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Location:
Annapolis, MDHighlights:
If you're seeking waterfront luxury and a legacy of maritime excellence, the Annapolis Yacht Club delivers. Founded in 1886 on the banks of Spa Creek, this premier private club offers world-class sailing, fine dining, and year-round social events—all in the heart of historic Annapolis.Recommended For:
Sailing enthusiasts, yachting families, competitive racers, and social members with a love for waterfront living.What I Love: ♥
A robust junior sailing program, elegant harbor-view dining, and a calendar filled with regattas, cruises, and club traditions.- Sail with one of the most competitive and respected racing fleets on the East Coast, or join relaxed cruising outings for both sailboats and powerboats.
- Train the next generation with a vigorous junior sailing program designed to build skills and confidence on the water.
- Dine in a beautifully appointed clubhouse offering award-winning cuisine, global wines, and panoramic views of Annapolis Harbor.
- Socialize all year long through member-exclusive events, educational activities, and winter programs tailored to all ages.
Cost:
Private membership required; inquire directly for rates and application details.Best time to visit:
Spring through fall for peak sailing season and waterfront events.Local tips:
The annual AYC regattas draw top-tier talent—check the club calendar if you want to catch the action (or participate!).How to Get to Annapolis Yacht Club:
From Washington, D.C. or Baltimore, take US-50 E to Rowe Blvd, then follow signs to downtown Annapolis. The clubhouse is located right on Spa Creek at the base of the Eastport Bridge.Address:
2 Compromise St, Annapolis, MD 21401Phone: 410-263-9279
Family-friendly Attractions
6. Unlock Canal Secrets at the C&D Canal Museum
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Location:
Chesapeake City, MDHighlights:
History and engineering buffs—this one’s for you. The C&D Canal Museum offers a fascinating look into the creation of the 14-mile Chesapeake & Delaware Canal, once a crucial maritime shortcut between two major bays.Recommended For:
Maritime history lovers, families, educators, and fans of engineering marvels.What I Love: ♥
Its authentic setting in an 18th-century pump house, interactive exhibits, and stories about one of the busiest shipping canals in the world.- Explore the history of a canal that revolutionized East Coast shipping, connecting Delaware Bay with Chesapeake Bay in the 19th century.
- Visit the museum housed in the original pump house—now on the National Register of Historic Places.
- Engage with interactive displays, videos, and hands-on exhibits showcasing the canal’s construction and legacy.
- Learn how the U.S. Army Corps of Engineers maintains and operates this vital waterway today.
Cost:
Free to visit; donations appreciated to support ongoing education and preservation.Best time to visit:
Spring through fall, when the canal-side walking and biking paths are also at their best.Local tips:
Pair your visit with lunch in charming Chesapeake City or a stroll along the canal-side trail right outside the museum.How to Get to the C&D Canal Museum:
From Baltimore or Wilmington, take I-95 to MD-213 South toward Chesapeake City. Follow signs to Bethel Road—the museum is located right at the canal in the heart of town.Address:
815 Bethel Rd, Chesapeake City, MD 21915Phone: 410-885-5622
7. Dig Deep at Calvert Cliffs State Park
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Location:
Lusby, MDHighlights:
Looking for fossils, fun, and some stunning shoreline views? Calvert Cliffs State Park in Southern Maryland is a prehistoric paradise just waiting to be explored. It’s a family-friendly favorite less than two hours from D.C. or Baltimore.Recommended For:
Fossil hunters, hikers, families, and beachcombers.What I Love: ♥
Ancient cliffs teeming with Miocene-era fossils, a peaceful sandy beach, and miles of wooded trails winding through scenic marshland.- Discover over 600 fossilized species—including shark teeth, seashells, and prehistoric marine life—dating back more than 20 million years.
- Explore 13 miles of hiking trails through freshwater marshes, forested terrain, and tidal wetlands.
- Enjoy the sandy beach, where kids and adults alike can search for fossils and splash in the gentle surf.
- Visit the recycled tire playground for a fun, eco-friendly pit stop, and don’t forget your fishing gear or picnic basket.
Cost:
$5 per vehicle for Maryland residents; $7 for non-residents. Fee collected at entry.Best time to visit:
Spring through early fall for pleasant weather and optimal fossil hunting.Local tips:
Bring a bucket or sifter for fossil collecting, and arrive early on weekends—parking fills fast.How to Get to Calvert Cliffs State Park:
From Washington, D.C. or Baltimore, take MD-4 South to Lusby. Turn onto HG Trueman Road and follow signs to the park entrance. Ample parking is available near the trailhead.Address:
10540 HG Trueman Rd, Lusby, MD 20657Phone: 443-975-4360
8. Paddle Through Time on the Captain John Smith Trail
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Location:
Chesapeake Bay region, HQ in Yorktown, VAHighlights:
If you're drawn to both history and the great outdoors, the Captain John Smith Chesapeake National Historic Trail delivers a one-of-a-kind journey. This 3,000-mile network of historic water routes traces the epic voyages of English explorer John Smith and his crew from over 400 years ago.Recommended For:
Paddlers, boaters, history lovers, educators, and outdoor explorers.What I Love: ♥
It’s the first national water trail in the U.S., combining natural beauty with stories of exploration, Native American heritage, and early American history.- Follow the exact paths John Smith took from 1607 to 1609 as he mapped the Chesapeake and connected with Native American communities.
- Explore the trail by kayak, canoe, or boat across rivers and tributaries that still hold the wild spirit of the 17th century.
- Learn about the trail's designation in 2006 as the first National Historic Trail to follow water routes—and one of only two National Historic Trails nationwide.
- Connect with cultural and interpretive sites along the route for insights into Indigenous history, colonial navigation, and the ecology of the Bay.
Cost:
Access to the trail is free, though some launch points and parks along the route may charge fees.Best time to visit:
Late spring through early fall for the best paddling conditions and interpretive programs.Local tips:
Start your planning with the official NPS maps and guides—this is not a single location but a web of connected waterways stretching through multiple states.How to Explore the Trail:
Access points span from Virginia through Maryland and into Pennsylvania. Launch a kayak at a nearby river, or visit one of the interpretive centers to learn more about the voyages of Captain Smith and the Bay’s early history.Address:
Yorktown, VA 23690Phone: 757-898-3400
9. Anchor Your Curiosity at the Chesapeake Bay Maritime Museum
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Location:
St. Michaels, MDHighlights:
If you're into boats, bays, and beautifully preserved maritime history, the Chesapeake Bay Maritime Museum is an absolute must. Located in the charming town of St. Michaels on Maryland’s Eastern Shore, it offers a deep dive into the Bay's nautical past and present.Recommended For:
History buffs, boat lovers, families, and hands-on learners.What I Love: ♥
The working boatyard, one-of-a-kind watercraft collection, and the chance to apprentice with real shipwrights—all set on a scenic waterfront campus.- Explore the largest collection of historic Chesapeake Bay watercraft, including drake-tail oyster boats, log canoes, and skipjacks.
- Experience a working boatyard where wooden vessels are restored using traditional methods—and you can even apprentice if you're up for it!
- Discover a historic lighthouse, butterfly garden, living shoreline, and exhibitions that tell the Bay's story from every angle.
- Stroll the museum’s waterfront grounds, once home to seafood packing houses and workboats, now transformed into a thriving hub of education and preservation.
Cost:
General admission varies by age; family and group rates available. Free for kids under 5.Best time to visit:
Spring through fall for outdoor activities and hands-on boatyard experiences.Local tips:
Grab lunch in downtown St. Michaels after your visit—it’s just a short walk from the museum and full of great seafood spots.How to Get to Chesapeake Bay Maritime Museum:
From Annapolis or Baltimore, take US-50 E across the Bay Bridge, then follow MD-33 into St. Michaels. The museum entrance is on Talbot Street along the waterfront.Address:
213 N Talbot St, St. Michaels, MD 21663Phone: 410-745-2916
10. Sip and Savor Along the Chesapeake Wine Trail
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Location:
Northern Neck & Middle Peninsula, VAHighlights:
If a weekend of wine, sunshine, and waterfront views sounds like your kind of getaway, the Chesapeake Wine Trail delivers. Winding through Virginia’s Chesapeake Bay region, this trail connects nine scenic wineries with tastings, tours, and unforgettable countryside charm.Recommended For:
Wine enthusiasts, couples, weekend travelers, and anyone looking to sip and savor by the bay.What I Love: ♥
Coastal vineyards, intimate tasting rooms, and farm-to-table pairings—all wrapped in Virginia hospitality.- Tour nine boutique wineries, each offering guided tastings, behind-the-scenes vineyard insights, and welcoming atmospheres.
- Taste a variety of vintages from refreshing whites to bold reds, many crafted with Virginia-grown grapes.
- Enjoy pairings with artisanal local fare, whether it’s oysters at The Dog and Oyster or a picnic at Ingleside Vineyards.
- Explore charming countryside stops like Caret Cellars, General’s Ridge, and Vault Field as you wind your way through the trail.
Cost:
Tasting fees vary by winery, typically $8–$15. Trail events may include bundled passes and specials.Best time to visit:
Spring and fall offer ideal weather and seasonal vineyard events; summer brings lively outdoor tastings.Local tips:
Plan ahead—some wineries require reservations for tastings or tours, and trail-wide passport events often include limited-time deals.How to Explore the Chesapeake Wine Trail:
Start in the Northern Neck or Middle Peninsula and map your route based on winery hours. Many stops are just a short scenic drive apart—perfect for a weekend wine tour with friends or a romantic escape.Address:
Caret Cellars, 495 Meadow Landing Lane, Caret, VA 22436Phone: 540-413-6454
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