Look carefully. Million-year-old shark teeth wash up here all day
long. The tiny horseshoe-shaped remains and other prehistoric sea
fossils are just part of the landscape at Bayfront Park, also known as
Brownie’s Beach to locals.

This spit of shoreline, south of Chesapeake Beach, is on the
peninsula known as Southern Maryland. It is just one of the area’s
archaeological treasure troves—and a part of the state often forgotten
by its northern neighbors.

Travelers will be well rewarded if they venture south past the
congestion of Annapolis and homogenous strip malls. Eventually,
cornfields and produce stands frame the pastoral merger of Routes 2 and
4, a central conduit through Maryland’s three southernmost counties:
Calvert, St. Mary’s, and Charles.

Surrounded by the Chesapeake Bay and Potomac and Patuxent Rivers, the
region offers more than unspoiled beaches and authentic seafood shacks.
Historically, this is the birthplace of our state, and the site of
several major battles and events from the 1770s to 1815—regarded as some
of the country’s defining struggles for freedom. It’s also a geological
find with prehistoric archaeological sites, eco-travel locales, and
some of the best aqua-sports trails in the state. Plan on a long weekend
to enjoy its charms.

A good place to begin exploring is Chesapeake Beach in the north end
of Calvert County. At one time, it was Maryland’s waterfront Shangri-La.
New-fangled, steam-engine trains brought tony Washingtonians in the
early 1900s to the posh coastal retreat to escape the summer heat in
D.C.

There was the fancy Belvedere Hotel and other resorts, pristine
salt-water beaches, a lively boardwalk, a glitzy casino, and numerous
restaurants. But during the Depression, trains changed their routes to
big cities and potential jobs. Soon, the town’s glory days faded away.

Recently, there has been a revival of sleepy Chesapeake Beach, which
is accessible via Route 261 from Route 2/4. The town has a wholesome
aura with a friendly main street of family-owned businesses, eateries
dishing up local fare, and a modest waterfront promenade with a crabbing
and fishing pier. Its active community of commercial fisherman, bait
and tackle shops, and charter-boat operators helps to preserve the
tranquil town from becoming a strip of chain stores.

While visiting, stay at the Chesapeake Beach Resort & Spa
(4165 Mears Ave., 866-312-5596), where rooms offer dazzling sunrise
views of the bay. The staff greets guests like new neighbors. Folks rent
kayaks, paddleboards, and canoes, or charter sailing and fishing
expeditions at the marina outside.

Have lunch next door at the family-operated Rod ‘N’ Reel Restaurant
(301-855-8351). The chatty wait staff will likely recommend a grilled
crabmeat sandwich—fresh crab imperial stuffed into a grilled cheese.
Afterward, walk off the calories by nosing around town.

Within a short distance is a water park, walking trails, and the
historic Chesapeake Railway Museum, housed in the original train depot.
Take the free trolley to North Beach to see its new boardwalk and its
beach with a large sandbar, as well as water sports, cafes, antique
shops, and the Bayside History Museum, exhibiting an original map from
Capt. John Smith’s exploration of the Chesapeake.

In the morning, take Route 261 south, where desolate beaches, like
Bayfront Park, provide an ideal spot to watch marine biologists and
archaeologists dig for fossils. Inland are some of Maryland’s few
remaining tobacco farms. Residents maintain that Maryland tobacco is
highly sought after because it burns more slowly.

Continue south to Jefferson Patterson Park and Museum
(10515 Mackall Rd., St. Leonard, 410-586-8501), a compound with
museums, a park, and hiking trails with more than 70 archaeological
areas dating from 9,000 years ago through Colonial times. The park
overlooks St. Leonard’s Creek, the site of the Battle of the Barges in
the War of 1812. It was here that Joshua Barney commanded a flotilla of
barges and gunboats against British forces, temporarily stalling the
British’s advance on Washington.

Throughout the 200th anniversary of the war this year, you can see
live reenactments of the battle and an interactive exhibit. There is
also a replicated Indian village depicting the sites that Capt. John
Smith encountered during his Chesapeake travels in 1608.

The park is also the headquarters of the Maryland Archaeological
Conservation Society, a clearinghouse for finds recovered from
land-based and underwater projects throughout Maryland’s history.
Definitely take the “Behind the Scenes” tour, which allows you to get up
close and personal with the archaeologists working on discoveries.

Next, backtrack to Running Hare Vineyard
(150 Adelina Rd., Prince Frederick, 410-414-8486), the largest of
Southern Maryland’s eight vineyards and wineries. Sample their
award-winning Chambourcin in the new Tuscan Tasting Room that overlooks
the vineyard.

Route 2/4 eventually leads to Solomons Island. Spend the night at the circa-1880 Back Creek Inn
(210 Alexander Ln., 410-326-2022). The rooms have water views and the
innkeeper provides complimentary bicycles for exploring. Peddle over to Annmarie Garden
(13480 Dowell Rd., 410-326-4640), a 30-acre indoor-outdoor sculpture
garden and arts center, with pieces on loan from the Smithsonian.
Continue to CD Cafe
(14350 Solomon’s Island Rd., 410-326-3877) for a fresh flounder
sandwich before heading to the Calvert Marine Museum, where the animated
“please touch” exhibits feature the area’s live and fossilized maritime
life. Don’t miss the resident sea otters, Bubbles and Squeak. End the
day with a water tour of Back Creek. The Patuxent Adventure Center (410-394-2770) delivers kayaks directly to the creek behind the Inn.

The next day, drive across the Governor Thomas Johnson Memorial
Bridge, which spans the lower Patuxent River, into Maryland’s oldest
county, St. Mary’s. This parcel features 400 miles of quiet shoreline,
8,000 acres of parkland, and countless hiking and bicycle trails,
perfect for any eco-enthusiast. History buffs will appreciate its role
as home to Maryland’s first colonists and the many ensuing battles.

The county is also home to Patuxent River Naval Air Museum
(22156 Three Notches Rd., Lexington Park, 301-863-7418). Here, you can
ride in an authentic flight simulator and view exhibits about early U.S.
astronauts and the testing of past U.S. naval aircraft.

Hollywood, MD, offers quite a different experience from its West Coast namesake. You’ll find Sotterley Plantation
(44300 Sotterley Rd., 301-373-2280), a property that is older than the
nation itself. It spans 300 years of tumultuous history: colonization,
revolution, slavery, and freedom. The 100-acre estate overlooking the
Patuxent River features a circa-1703 Tidewater manor house, an 1830s
slave cabin, and 17 historic outbuildings.

More history awaits in Leonardtown, one of the nation’s oldest county
seats. Established in 1708, it has survived a turbulent past: British
troops raided it during the Revolutionary War and the War of 1812; Union
soldiers occupied it during the Civil War. Visit the circa-1744 Tudor Hall (41680
Tudor Pl., 301-475-2467), once the home of Francis Scott Key’s uncle
Phillip and now St. Mary’s County Historical Society. Nearby is the
quirky 1858 Old Jail Museum with its cells and a cannon from the ship of
Maryland’s first settlers.

Have lunch outdoors, weather permitting, at Café des Artistes
(41655 Fenwick St., 301-997-0500), whose chef sources local ingredients
for dishes like oysters café, featuring oysters on the half shell
topped with crab, provolone, spinach, and shallots. Then, check out the
avant-garde shops along Fenwick Street selling chocolate, jewelry,
kitchen and culinary products, local art, and rare books.

It’s a short drive to the Port of Leonardtown Public Park. Visit the
resident winery, a cooperative of independent Southern Maryland
winemakers, whose products are aged, bottled, sampled, and sold on-site.
At the park, you can rent a canoe or kayak and paddle along McIntosh
Run and its 58-acre Forest Interior Dwelling Species Habitat to view
native bald eagles, wild turkeys, Baltimore Orioles (the feathered
ones), and more.

Head to the Island Inn & Suites
(1610 Piney Point Rd., 301-994-1234) on St. George’s Island (about 12
miles from Leonardtown) in time to watch the sun dip into the Potomac
from the Adirondack chairs of your private balcony. Don’t let the modest
motel-ish exterior fool you. Inside are grand, cushy accommodations
with luxurious bathrooms. For dinner, try the garlicky bistro mussels
and a blackened rockfish sandwich on the sunset deck at the Inn’s Island
Bar & Crab House.

In the morning, borrow a kayak (gratis) from the hotel and paddle
around the island, exploring its remote, rugged beaches. Founded in
1634, it was the site of Maryland’s first Revolutionary War battle.
During the War of 1812, the British made the island their headquarters,
raiding nearby shipyards and river plantations. Today, it encompasses
the vacation homes of fishermen and the Chesapeake Bay Field Lab (16129 Piney Point Rd., 301-994-2245), where you can learn to dredge for oysters aboard an authentic skipjack.

By car, drive south on Route 5 to Point Lookout Road. Stop at Buzzy’s Country Store
(12665 Point Lookout Rd., Scotland, 301-872-5430), a vestigial
throwback with bait, beer, and sandwiches. Load up on provisions and
continue to the 1,000-acre Point Lookout State Park (11175
Point Lookout Rd., 301-872-5688) and Lookout Point, Maryland’s
southernmost tip. (It was the location of a prison camp for Confederate
soldiers in 1863.) Now, there are serene beaches, land and water trails,
a nature center, and endless views of the confluence of the Chesapeake
and the Potomac.

Take Point Lookout Road back to St. Mary’s City. This 800-acre
outdoor “living museum” is Maryland’s first capital and one of the
best-preserved Colonial towns in the U.S. Interpreters in 17th-century
attire reenact colonist life on a still-working tobacco plantation.
Visit Farthing’s Ordinary gift shop (18751 Hogaboom Ln., 240-895-2088) for reproduction Colonial glassware.

Have dinner at Scheibles Restaurant
(48342 Wynne Rd., Ridge, 301-872-0025), a classic seafood dive known
for its local fish and oysters. Stay overnight in an elegant waterfront
cottage at Woodlawn B&B
(16040 Woodlawn Ln., Ridge, 301-872-0555), whose grounds were part of
Trinity Manor, one of the original colonist settlements. Interesting
fact: The house’s original front door is on the backside of the house,
facing the water, since that is how visitors arrived in Colonial times.
Ask for a house tour from husband-and-wife innkeepers Jim Grube and
Maggie O’Brien, a past president of St. Mary’s College of Maryland.
Before bed, try a glass of sparkling White Shoals from the on-site
winery.

After breakfast, drop by the aqua farm Circle C Oyster Ranch (49676 Freemans Rd., Dameron, 301-872-4177) to see the floating oyster reef—and pick your own oysters!

You’ll also want to visit the St. Clement’s Island-Potomac River Museum
(38370 Point Breeze Rd., Colton’s Point, 301-769-2222). The exhibits
depict Maryland’s first colonists landing on St. Clement’s Island in
1634, in search of religious freedom. Catch the water taxi for another
view of the island.

Before heading home, pick up local produce and other treats at the North St. Mary’s County Farmers Market (37600
New Market Rd., Charlotte Hall, 301-475-4200, ext. 1402). Southern
Maryland’s famous stuffed ham sandwich is a must-have. The recipe is
said to have been created by plantation slaves.

After savoring the flavors of the area, you’ll want to return soon.
After all, there are still adventures to be had in Charles County.