1. Hunt for fossils at Calvert Cliffs
Nothing ruins a trip to Maryland’s Western Shore like a shark big enough to swallow a rhino. Luckily, the megalodon shark (with its 7-inch-long teeth) went extinct about 2.5 million years ago, but you can still find its fossilized remains at Calvert Cliffs. You don’t want to dig directly into the cliffs — it’s dangerous and illegal — but you can pan for shark teeth on the shore. One popular access point is Brownie’s Beach at Bay Front Park in Calvert County, Md., which charges $5 to $18 per person. Or go on a guided tour with the Calvert Marine Museum (14200 Solomons Island Road, Solomons, Md.). S.D.
Food and drink
2. Have a pint (or two) at Burley Oak Brewing
If you’re into craft beer, you’ve likely seen Burley Oak Brewing Company’s hoppy ales and tart sours on draft lists or in cans in D.C. and Maryland. Visit the rustic taproom in the small town of Berlin, Md. (population: less than 5,000), and you’ll get to sample whatever’s fresh — just don’t go in expecting to try any one specific beer. Burley Oak doesn’t stick to flagships: They brew whatever they want, when they want. (On Saturday, however, you can stop by for the release of a new canned offering, the piney and juicy Sequoia Sap IPA, which sounds like fall in a glass.) Not into beer? They also make their own cold-brew coffee and, for the kids, handcrafted sodas. R.G.
Burley Oak Brewing Company, 10016 Old Ocean City Blvd., Berlin, Md.; open Mondays-Thursdays, 11 a.m.-11 p.m., Fridays and Saturdays, 11 a.m.-2 a.m., and Sundays, 11 a.m.-9 p.m.
Food and drink
3. Drink (good) beer from Maryland’s Eastern Shore
There’s plenty of good beer to be found on the Eastern Shore, so while the two-day Good Beer Festival’s name is a little obvious, you have to appreciate the organizers’ desire to get right to the point. A showcase for more than 10 Eastern Shore breweries — including Evolution, Tall Tales, Backshore and Assawoman Bay — the festival in Salisbury, Md., also includes dozens of beer-makers from across the country (Ballast Point, Lagunitas), other parts of Maryland (RAR, The Brewer’s Art) and D.C. (Right Proper). A ticket gets you a 3-ounce tasting glass and access to as many samples as you choose. Kate Mills, The Pocket Band and Uprizing are among the musicians performing during the festival. R.G.
Pemberton Historical Park, 5561 Plantation Drive, Salisbury, Md.; Sat. & Sun., 12:30-6:30 p.m., one-day tasting ticket: $35, non-tasting: $10.
4. Hike, bike and watch for ponies on Assateague Island
Rest assured, your trip to Assateague Island will be relaxing, because the most action-packed three minutes of the island’s year — when tourists gather to see the wild ponies swim across the Assateague Channel — happened in July. For your fall getaway, safely admire the ponies from afar and enjoy the 37 miles of beaches, winding hiking trails and hunting, if you’re so inclined. It’s best to plan your camping trip early: All of the 100 or so campsites are fully booked during the weekends this season, but weekday spots are still available. L.M.
Assateague Island Visitor Center, 11800 Marsh View Lane, Berlin, Md.
5. Stop for local snacks at the Bartlett Pear Inn
It’s worth setting a course for the Bartlett Pear Inn and its farm market on your fall road trip, even if it’s just to break your diet of Slim Jims and gummy worms. Stock up on local cheeses, homemade breads and jarred preserves and pickles. If the quiet coastal town of Easton or the inn’s seven cozy rooms (all pear-themed) don’t convince you to stay, the complimentary breakfast made with local Chesapeake Bay ingredients (not pear-themed) just might. L.M.
28 S. Harrison St., Easton, Md.
6. Build a boat (or just watch) at the Chesapeake Bay Maritime Museum
We get it: When you’re in a beautiful seaside town like St. Michaels, Md., a museum sounds like something a mean high school teacher from a ‘90s movie would suggest. But at this 18-acre campus dotted with small buildings, you can enjoy the fresh air while you explore what life was like for Marylanders in decades past. Play lighthouse keeper, tong for oysters and watch the shipwrights build wooden boats. If you’re considering parlaying your visit into a career, sign up for one of the museum’s workshops, which promise to turn you into a master woodworker, tool sharpener or boat builder. L.M.
213 N. Talbot St., St. Michaels, Md.
7. ‘Rocky’ out at the Chesapeake Film Festival
Think film festivals are just for the snooty? Not the Chesapeake Film Festival. This year, the festival is giving its first lifetime achievement award to John G. Avildsen, director of such films as “Rocky” and “The Karate Kid” … and “Rocky V” and “The Karate Kid Part III.” He’ll be around for a Q&A after a screening of his “Lean on Me” on Saturday, and he’ll be taking in a karate demonstration after the showing of “The Karate Kid” that same day. There will also be documentaries, shorts, features, more Q&A sessions and panel discussions. K.P.K.
Easton, Md.; Oct. 27-30.
Food and drink
8. Sugar up the kids (or yourself) at Durding’s Store
MOM DAD MOM DAD CAN WE GET SOME ICE CREAM LOOK THEY HAVE MILKSHAKES AND SUNDAES AND FLOATS AND THE SAME FAMILY HAS OWNED THIS BUSINESS FOR THREE GENERATIONS AND THEY ALSO HAVE OTHER FOOD LIKE SANDWICHES AND THE SODA FOUNTAIN DATES FROM 1935 CAN WE STOP CAN WE STOP CAN WE STOP CAN WE CAN WE CAN WE?! K.P.K.
Durding’s Store, 5742 N. Main St., Rock Hall, Md.
9. Get squirrely at the Blackwater National Wildlife Refuge
Come for the birds, stay for the squirrels. Established in 1933 as a refuge for migratory waterfowl, Blackwater National Wildlife Refuge has 25,000 acres of trails, trees and water (in fact, one-third of Maryland’s tidal wetlands are within the refuge). In addition to waterfowl, you can see deer, bald eagles and the largest population of the formerly endangered Delmarva Peninsula fox squirrel. Visitors can hike, bike, drive or boat on the various trails; the visitor center is a prime place to scope for bald eagles, and there are cameras offering live views of osprey and eagle nests. Hunting and fishing are options in the proper season and with the proper permits. K.P.K.
Blackwater National Wildlife Refuge, 2145 Key Wallace Drive, Cambridge, Md.; $3 per vehicle.
10. Embrace opulence at Mount Harmon Plantation
Drown in real estate envy with a tour of Mount Harmon Plantation’s centerpiece, a really, really, really big house restored to its late-18th-century appearance. A former tobacco plantation, Mount Harmon sits on 200 acres and includes a Georgian manor house, a colonial kitchen, a formal boxwood garden and a tobacco prize house, where the leaves were treated before being packed into barrels and shipped overseas. The Revolutionary War and Colonial Festival, featuring battle re-enactments, a colonial marketplace and all the breeches you can shake a stick at, is coming up on Oct. 29 and 30. K.P.K.
Mount Harmon Plantation, 600 Mount Harmon Road, Earleville, Md.; Thursdays-Sundays, 10 a.m.-3 p.m., through Oct. 31, $10
Food and drink
11. Watch the experts at Smith Island Crabmeat Co-Op
Anyone who’s ever picked a crab can tell you it’s not the most efficient way to get a meal (though having a beer or four certainly makes the experience more pleasant). Stop by Smith Island Crabmeat Co-Op to see professionals strip those little blues for everything they’re worth. You can peer through a window or, for $3, step into the picking area to ask questions and snag a sample. K.P.K.
Smith Island Crabmeat Co-Op, 123 Wharf St., Tylerton, Md.; open daily through November, 8-10 a.m. and 5-7:30 p.m.
12. Get bird-brained at the Waterfowl Festival
Have a ducking good time at the three-day event that celebrates every ducking waterbird you can ducking think of. Painters, photographers and decoy makers will show off their wares; other draws include classes and lectures, dog demonstrations, kids activities and waterfowl-calling contests. In fact, this year is the World Goose Calling Championship, which happens every five years — winners from the past five annual contests return to battle one another for fame, glory and the pride of leading around 15 or 20 very confused geese for the rest of the evening. K.P.K.
Waterfowl Festival, various locations, Easton, Md.; Nov. 11-13, three-day pass: $15.
13. Go birding at the Chesapeake Bay Bridge-Tunnel islands
For vacationing families and migrating birds crossing the Chesapeake Bay, Sea Gull Island has long served as a much-needed place to rest and refuel. This rocky spot, 3.5 miles from Virginia Beach, is one of four man-made islands that connect the tunnels of the Chesapeake Bay Bridge-Tunnel to its spans. Sea Gull Island (officially known as One Island on the Bay) is the only one always open to the public: There, you can have a bite at the Chesapeake Grill and scope out some rare birds. Grab your binoculars and scan for rafts of sea ducks, which begin arriving in the fall and spend the winter bobbing in the toasty bay before returning to the Arctic tundra to breed. But go soon: Starting Oct. 1, 2017, Sea Gull Island will be closed for five years. S.D.
14. Visit Kiptopeke State Park and its concrete shipwrecks
Could the stuff of sidewalks be good boat-building material? The answer is no, but that didn’t stop the Navy from building concrete ships when steel was scarce during World War II. These thick-hulled behemoths served honorably in the war, only to be scrapped and used to create a breakwater at Kiptopeke State Park. You can see them from the shore, but for the best look, rent a kayak. SouthEast Expeditions (southeastexpeditions.com) rents out kayaks year-round, and they will deliver one to the pier for you ($40/half-day). Just a five-minute paddle from shore, the breakwater is a favorite haven for all sorts of fish, so bring your gear (and valid Virginia saltwater fishing license) and you might end up lugging a 50-pound striped bass back to shore. S.D.
3540 Kiptopeke Drive, Cape Charles, Va.
Food and drink
15. Eat historically significant ice cream at Doumar’s Cones and Barbecue
In 1904, Syrian immigrant Abe Doumar was selling tchotchkes at the St. Louis State Fair when he noticed that a nearby ice cream stand had to close when it ran out of paper dishes. He bought a waffle from a waffle stand, rolled it up like Middle Eastern flatbread and plopped some ice cream inside, creating the first waffle cone. Others have claimed the invention, but one of Doumar’s original machines is still pumping out waffle cones at Doumar’s Cones and Barbecue. Stop by and chat with one of Doumar’s descendants, grab an ice cream cone or go really old-school and order one of the award-winning sundaes in a proper glass dish. S.D.
1919 Monticello Ave., Norfolk, Va.
16. Rock out at The NorVa
Think of The NorVa as the 9:30 Club of Virginia. A former vaudeville theater that opened in 1917 (and later became a movie theater), The Norva gets many of the same high-caliber acts as the vaunted D.C. club, in a similarly intimate setting (capacity: 1,450). Since the downtown Norfolk club opened its doors with headliner James Brown in 2000, Bob Dylan, Justin Timberlake and Prince have also graced its stage. This fall’s lineup offers an eclectic mix of acts, including reunited new-wave band Squeeze (Monday), rap duo Rae Sremmurd (Oct. 23), indie-rockers Band of Horses (Oct. 26) and Richmond metal legends Gwar (Oct. 27). Want to get a good view of the stage? Eat at the nearby FM Restaurant (320 Granby St.) and you can enter the venue 15 minutes before doors. R.G.
NorVa, 317 Monticello Ave., Norfolk, Va.
Food and Drink
17. Sample local wines on the Chesapeake Bay Wine Trail
Go ahead and draw straws to pick a designated driver now: The 10 wineries of the Chesapeake Bay Wine Trail are spread out across the Northern Neck of Virginia, about 90 minutes from one end to the other. For maximum drinking-to-driving ratio, stick to the trail of four wineries in the southeast, each located 10-15 minutes from the next. Start at Athena Vineyards (3138 Jessie Dupont Memorial Highway, Heathsville, Va.) and head south, stopping at Jacey Vineyards (619 Train Lane, Wicomico Church, Va.) and Good Luck Cellars (1025 Good Luck Road, Kilmarnock, Va.). End your day at the Dog and Oyster Vineyard (170 White Fences Drive, Irvington, Va.), where you can sleep it off at the winery’s bed-and-breakfast built in a turn-of-the-century schoolhouse. Feeling more ambitious? Plan your trip for Nov. 12 and 13, when eight of the wineries will be participating in a Fall Oyster Crawl. L.M.
18. Plan a Dogfish Head-centric beer-cation
In 2014, Dogfish Head Brewery expanded its craft beer empire with a cozy inn in Lewes, Del. — about 11 miles from the brewery in Milton, Del., and 6 miles from the company’s Rehoboth Beach, Del., brewpub. The rooms at the Dogfish Inn have several beer-centric design touches — including bottle openers on the walls — but, oddly, you can’t actually buy beer there. Instead, you’ll have to grab a six-pack or growler fill from the brewery (or from one of the shops in Lewes). The inn offers add-on packages, like the $45 All-INNclusive Experience, featuring an expansive tour of the brewery, a tasting and transportation to the brewery and the brewpub. R.G.
Dogfish Inn, 105 Savannah Road, Lewes, Del.
19. Try your luck at Dover Downs
Think of Dover Downs Hotel & Casino as Disney World for adults: a giant playground full of ways to tire you out until bedtime. There are nine restaurants, five bars, a spa, a horse-racing track and a 1-mile motor-racing track. In addition to the year-round activities, the hotel hosts musicians and comedians — this month Tracy Morgan (Oct. 14) and the Glenn Miller Orchestra (Oct. 28) will perform. L.M.
1131 N. Dupont Highway, Dover, Del.
More ways to enjoy D.C.: