63rd Annual Hard Crab Derby and Fair. Go crazy for crabs with cooking contests, crab picking competitions, boat races, crafts, carnival rides, and kids’ activities. Somers Cove Marina, Crisfield, Md. 410-968-2501, http://www.crisfieldheritagefoundation.org
Four under Forty. The exhibit features the work of four Kent County resident artists, all in their fourth decade and at the prime of their creative lives. Robbi Behr, Emily Kalwaitis, Joe Karlik and Angela Ranzoni present pieces that challenge and reveal things normally not considered. Chestertown Arts League, Chestertown, Md. Opening reception, Sept. 3, 5-8 p.m. 410-778-5789, http://www.chestertownartsleague.org
51st Annual Skipjack Race and Festival. Head to Deal Island for the Blessing of the Fleet, skipjack race, a parade, car show and live music. Gospel concert on Sat. 6 p.m.; Races on Monday, 9:30 a.m.. Deal Island, Md. 410-784-2799, http://www.webauthority.net/lions.htm
Maryland Seafood Festival. Join 20,000 other seafood lovers and chow down on bounty from the Bay. Performers include the Kelly Bell Band and the Rob Levit Trio. Sandy Point State Park, Annapolis. http://www.mdseafoodfestival.com
Arts Alive 12! The Maryland Hall for the Creative Arts hosts its annual fundraising event featuring silent and live auctions, tasting stations from area restaurants and caterers, and entertainment by the Brooks Tegler Orchestra. Honorary chairs of the event include Gov. Martin O’Malley, Congressman John Sarbanes, and Speaker of the House Michael Busch. Maryland Hall for the Creative Arts. 6-11 p.m. 410-263-5544, http://www.marylandhall.org.
23rd Annual Duck Fair. Thirty carvers, collectors, and artists display and sell their works. Havre de Grace Decoy Museum, Havre de Grace, Md. 9 a.m.-3 p.m. 410-939-3739, http://www.decoymuseum.com
Old-time Baseball. Players sport authentic uniforms and play with bats, balls, and bases from the 1860s. Steppingstone Museum, Havre de Grace, Md. Noon.
410-939-2299, http://www.steppingstone-museum.org
Paws for a Cause Charity Night & Silent Auction. Help your furry friends at The Humane Society of Harford County and Luna’s House! Enjoy the 5th annual charity night hosted by Paws for a Cause and participate in or donate to the silent auction. Teavolve Cafe and Lounge. Baltimore. 6:30-9:30 p.m. 410-732-2633, http://www.paws4cause.org
Artsfest. Stop by for a weekend featuring more than 100 artists, live music, food, and fine brews at the beautiful Annmarie Garden Sculpture Park. Solomon’s Island, Md. 10 a.m.-5 p.m. 410-326-4640, http://www.annmariegarden.org
Summer Sendoff: Blues, Brews, and BBQs. Bid summer adieu at a street festival featuring live music, art exhibits, and finger lickin’ barbecue aplenty. Downtown Cambridge, Md. 5-9 p.m., 410-228-0020, http://www.cambridgemainstreet.com
9th Annual Paint Annapolis. Thirty of the nation’s top plein-air artists paint throughout Annapolis for three days, competing for the grand prize. Maryland Hall and streets of Historic Annapolis. 410-263-5544, http://www.paintannapolis.com
Sunfest. Don’t miss Ocean City’s biggest festival, featuring arts and crafts, food, live entertainment, and hayrides and games for kids. Inlet Lot, Ocean City, Md. Thu-Sat 10 a.m.-10 p.m.; Sun 10 a.m.-6 p.m. 800-626-2326, http://www.ococean.com
Chesapeake Film Festival. Take a break from summer blockbusters with artistic documentaries, narratives, and short films. Then, mingle with the filmmakers. Easton, various locations. 410-822-5089, http://www.chesapeakefilmfestival.org
Berlin Fiddler’s Convention. Fiddlers from around the country compete for four-string supremacy. The event kicks off with a concert on Friday night, followed by an acoustic music competition all day Saturday and closes with a bluegrass gospel jam on Sunday morning. Berlin, Md., 410-641-4775, http://www.berlinchamber.org
Rock Hall FallFest. Join the town of Rock Hall for a street fair with artisans, 50 craft booths, two stages of music, food, children’s activities, and waterfront exhibits. The Mainstay, Rock Hall, Md. 10 a.m.-5 p.m. 410-778-0416, http://www.mainstayrockhall.org/fallfest
Waterfront Festival and Cardboard Regatta. Head to the Chester River for tours, boating, sailing, kayaking, and the Cardboard Boat Regatta. Plus, music by Chester River Runoff, pony rides, and food. Wilmer Park, Chestertown, Md. 12-4 p.m. 410-778-7295, http://ces.washcoll.edu
Fall Harvest Festival and Craft Show. Get an early start on Halloween with scarecrow making and pumpkin painting. Also enjoy clogging and square dancing, a straw maze, food and crafts. Steppingstone Farm Museum, Havre de Grace, Md. 11 a.m.-5 p.m. 410-939-2299, http://www.steppingstonemuseum.org
Kinsale Regatta. The Northern Neck Sailing Association hosts its third annual Kinsale Regatta event, featuring a “round the buoys” race, cash bar and reception on Saturday and a pursuit race on Sunday. Proceeds benefit the Smith Point Sea Rescue. Port Kinsale Marina, Kinsale, Va. Tickets, $65 per boat. http://www.nnsa-sailing.com
St. Mary’s Century Bike Ride. Whip out your bicycles and tone up those muscles for an all-day, 100-mile bicycle tour through scenic St. Mary’s County. Cyclists of all skill levels ride the charming back roads of the rural town, with rest stops stocked with snacks, refreshments and local specialties. College of Southern Maryland, Leonardtown, Md. 7 a.m. Registration, $40. 301-475-4200, http://www.paxvelo.com
Winefest on the Beach. Taste reds and whites from the finest wineries in the Mid-Atlantic region, as well as Chesapeake cuisine and microbrews. Inlet parking lot, Ocean City, Md. noon-7 p.m. 410-280-3306, http://www.winefest.com
Harbor Day at the Docks. Celebrate the history and heritage of local maritime traditions with educational exhibits, live music, local seafood, cooking demonstrations, seafaring competitions, children’s games and more. Don’t miss walking tours of a working Coast Guard ship. Commercial Fishing Harbor, West Ocean City, Md. 10 a.m.-5 p.m. Free. 410-289-6733, http://www.ocharborday.com
United States Sailboat Show. Check out the nation’s oldest and largest in-water sailboat show. Expect new racing and cruising boats on sale, plus equipment, rigging, and more. Annapolis City Dock and Harbor, Annapolis.410-268-8828, http://www.usboat.com
Chesapeake Wildfowl Expo. Wildlife meets art with carving competitions, antique decoys, and auctions. Chow down at the pig roast and chicken barbecue. Ward Museum of Wildfowl Art, Salisbury, Md. Fri. 10 a.m.-6 p.m.; Sat. 9 a.m.-5 p.m. 410-742-4988, http://www.wardmuseum.org
Ocean City Oktoberfest. Eat drink and be merry with music, dancing, sing-a-longs, German food, and “bier.” Ocean City Convention Center on 40th Street, Ocean City, Md. Fri.-Sat. 11 a.m.-11 p.m.; Sun. 11 a.m.-11:30 p.m. 410-524-7020, http://www.oceanpromotions.info
Chestertown Book Festival. The second annual book fest features a gathering of authors at various bookstores, libraries, hotels, and inns throughout Chestertown and Washington College. Check the website for exact locations. http://www.chestertownbookfestival.org
Chesapeake Wildfowl Expo. See the parking lot of the Salisbury University’s wildfowl art museum transform into a marketplace for fine antique decoys, collectible hunting items, folk art and antique furniture. Come out for the pig roast on Friday and carving contests and competitions on Saturday. Ward Museum of Wildfowl Art, Salisbury, Md. Free admission. 410-742-4988, http://www.wardmuseum.org
3rd Annual Graw Days Festival. Commemorate the famous Havre de Grace racetrack, with Roaring ’20s period costumes and ragtime music. Downtown Havre de Grace, Havre de Grace, Md. 10 a.m.-5 p.m. 410-939-1811, http://www.mainstreethdg.com
Chincoteague Oyster Festival. Mark the arrival of oyster season with bivalves prepared all ways. Maddox Family Campground, Chincoteague Island, Va. 10 a.m.-4 p.m. 757-336-6161, http://www.chincoteaguechamber.com
Patuxent River Appreciation Days. This annual festival includes science and history exhibits, a craft fair, music, and free harbor cruises. Calvert Marine Museum, Solomon’s Island, Md. 10 a.m.-5 p.m. 410-326-2042, http://www.pradinc.org
Olde Princess Anne Days. Activities include a historic house and garden tour, crafts, military encampment, music, and children’s activities. Teackle Mansion, Princess Anne, Md. 410-651-2238, http://www.teacklemansion.org
4th Annual Boat Show Bash. Put on your sailor’s hat and celebrate the upcoming U.S. Sailboat Show by eating, drinking, and dancing the night away. The Eastport Yacht Club hosts this outdoor dance party, supporting the EYC Foundation and Box of Rain with some of the proceeds. Eastport Yacht Club Sycamore Point. Annapolis, Md. 6:00-11:00 p.m. 410-263-8733, http://www.eastportyc.org.
United States Powerboat Show. It’s just like the sailboat show—but for the powerboat crowd! Annapolis City Dock and Harbor. 410-268-8828, http://www.usboat.com
The Rocky Horror Show. Do the “Time Warp Again” at this live production of the infamous cult flick. Church Hill Theatre, Church Hill, Md., 410-758-1331, http://www.churchhilltheatre.org
Crabtoberfest. German meets Eastern Shore tradition with dancing, an authentic biergarten, bratwurst, and tons of crabs. Sailwinds Park, Cambridge, Md. Noon-sunset. http://www.crabtoberfest.com
Autumn Wine Festival. Savor wine from 20 Maryland wineries. Pemberton Historical Park, Salisbury, Md. Sat. 11 a.m.-6 p.m.; Sun. 12:30-6 p.m. 410-548-4914, http://www.autumnwinefestival.org
Concert of Stars. Break out the opera glasses for a night of Italian arias and duets. Annapolis Opera presents the Met’s Jason Stearns along with the return of Annapolis favorites Jonathan Burton and Colleen Daly conducted by Ron Gretz. St. John’s College, Annapolis, Md. 8:00 p.m. 410-267-8135.
Downrigging Weekend. Ships from across the Mid-Atlantic make their way up the Chester River to participate in the schooner Sultana’s 10th annual downrigging event. Come check out the fleet of tall ships and historic vessels, live entertainment, and food galore. Chestertown, Md., 410-778-5954, http://www.sultanaprojects.org
Artworks Studio Tour. Visit more than 30 studios and homes in Chestertown, Kent, and Queen Anne’s counties. 9 a.m.-5 p.m. 410-778-6300, http://www.artworkschestertown.org
World Championship Punkin Chunkin. How far can you chuck your pumpkin? Competing teams from around the world construct hurling devices (catapults, cannons, etc.) to see who can hurl their pumpkin the farthest. Chaplin’s Chapel Rd., Nassau, Del. 7:30 a.m. http://www.punkinchunkin.com/main.htm
Urbanna Oyster Festival. Tempt your taste buds at Virginia’s official oyster festival. Urbanna, Va. Fri. 9 a.m.-midnight.; Sat. 9 a.m.-6 p.m. 804-758-2613, http://www.urbannaoysterfestival.com
Art-Cessories. This holiday-season exhibit features an installation of wearable, functional artworks by regional artists. Main Street Gallery, Cambridge, Md. 443-477-3699, http://www.cambridgemainstreet.com
Rehoboth Beach Independent Film Festival. View more than 100 American and international features, documentaries, and shorts. The Movies at Midway, Highway 1, Downtown Rehoboth, De. 302-645-9095, http://www.rehobothfilm.com
Waterfowl Festival. The perfect event for sportsman and art lover alike, featuring crafts, live music, and food. Throughout Easton, Md. Fri-Sat 10 a.m.-6 p.m.; Sun 10 a.m.-4 p.m. 410-822-4567, http://www.waterfowlfestival.org
Assateague Island Waterfowl Weekend. Embark on special guided walks and tours at the peak of migration. Chincoteague National Wildlife Refuge, Chincoteague, Va. 6 a.m.-6 p.m. 757-336-6122, http://www.chincoteaguechamber.com
Christmas on the Square Celebrate Black Friday with music, food, and a tree lighting. Leonardtown, Md. 301-475-9791, http://www.leonardtown.somd.com
47th Annual Holly Ball. Have a ball for a good cause while you enjoy cocktails, dinner, and dancing to the live music of Oracle. The ball features a silent auction, luxury vendors, and complimentary photographs. Proceeds support the Anne Arundel County Food and Resource Bank and other local charities.Sheraton Hotel. Annapolis, Md. 6-11 p.m. 410-263-1750, http://www.severntownclubhollyball.com
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