Oct. 31-Nov. 2
The schooner Sultana welcomes the Bay's tall ships and historic vessels to join her in Chestertown, Md., to end the sailing season with a weekend full of dockside tours and public sails, a wooden boat show, fireworks and plenty of other activities throughout the weekend. Chestertown, Md. 410-778-5954; www.sultanaprojects.org.
Caribbean 1500 Start and Race
Boats heading to Tortola, BVI, will depart from Portsmouth's Ocean Marine Yacht Center to rally and race south to the Caribbean. Group start is scheduled for noon on Nov. 2. 757-788-8872; www.worldcruising.com.
Urbanna Oyster Festival
Urbanna's annual bivalve fest is one of the biggest on the Bay and will feature oysters (of course), two parades, a shucking contest, arts and crafts vendors, live entertainment and wine tastings. Urbanna Va. Fri. 10 a.m.-7 p.m.; Sat. 9 a.m.-5 p.m. 804-758-0368; www.urbannaoysterfestival.com.
Colonial Beach Rockfish Tournament
This annual rockfish tournament features over $10,000 in prize money and two days of great fishing. Colonial Beach, Va. Sat.-Sun. Fishing 7 a.m.- 4 p.m. 804-224-5000; www.rockfishtournament.org.
Enjoy an evening of gallery openings and receptions, late retail shopping, live music, restaurant deals and more. Downtown Cambridge, Md., 5-9 p.m., 443-477-0843; www.cambridgemainstreet.com.
Cheer on the tuggers or don your sailing gloves and join in the annual tug-of-war across Spa Creek, pitting Annapolis against the feisty Maritime Republic of Eastport. Before and after the tugging, enjoy live music, food and fun on both sides of the creek. 10:30 a.m.-4 p.m.; the tugging begins at the "crack of noon." www.themre.org.
Reedville Oyster Roast
Get your tickets early for this all-you-can-eat extravaganza of oysters, bean soup, clam chowder and more, as it routinely sells out. The food, music, dancing and fun all benefit the Reedville Fishermen's Museum. Reedville, Va. 2-5 p.m. 804-453-6529; www.rfmuseum.org.
Fish For A Cure
Anglers will raise money for the Anne Arundel Medical Center's Geaton and JoAnn DeCesaris Cancer Institute, then head out for a day of fishing for rockfish and perch, capped with a festive after-party at Pusser's. Annapolis. Fishing sunrise to 5 p.m. 410-349-4070; www.fishforacure.org.
With extended hours for the holidays, the Yorktown Riverwalk Landing will be busy with shoppers stocking up on local produce, fresh seafood and baked goods, plus holiday treats and gifts, all while enjoying live entertainment. Riverwalk Landing, Yorktown, Va. 9 a.m.-3 p.m. 757-890-3500; www.yorkcounty.gov/tourism.
The town of Easton, Md., will be aflock with wildlife art, including over 300 artists' wildlife paintings, carvings, decoys and photography. There will also be calling contests, retriever and fly-fishing demonstrations and more. Easton, Md. Fri.-Sat. 10 a.m.-6 p.m.; Sun. 10 a.m.-4 p.m. 410-822-4567; www.waterfowlfestival.org.
This inaugural rockfish tournament boasts a $100,000 prize for a Maryland state record fish (currently 67.8 pounds) and a $10,000 prize for the first rockfish weighing more than 55 pounds. There will also be other cash prizes, a kick-off happy hour party, a post-tournament party and more, all to benefit the Bowen Foundation for Autism. Chesapeake Harbor Marina, Annapolis. Fishing 7 a.m.-4 p.m. 410-268-1969; www.rocksgiving.com.
Calvert Marine Museum Concert-Bumper Jacksons
Head to the Calvert Marine Museum for the last concert of the season, featuring the Bumper Jacksons, a popular swing, blues and old-time country band performing the traditional sounds of America. Calvert Marine Museum, Solomons, Md. 410-326-2042; www.calvertmarinemuseum.com.
Casey Neal Rogers Rockfish Tournament
This rockfish challenge will feature a $5,000 first prize and benefit the Casey Neal Rogers memorial scholarship fund. An awards dinner open to the public will follow. Smith Point Marina, Reedville, Va. Fishing 7 a.m.-3 p.m., awards dinner to follow. 804-453-4077; www.cnrtournament.com.
Grand Illumination Parade
Kick off the holiday season in Norfolk with the city's 30th annual celebration, including a grand parade, lighted floats, marching bands and Santa, and the lighting of the Norfolk and Portsmouth skylines for the holiday season. Norfolk. 7 p.m. 757-623-1757; www.downtownnorfolk.org.
MSSA Fall Classic
Anglers across Maryland's waters will vie for nearly $100,000 in prizes during the Maryland Saltwater Sportfishermen's Association's annual fall tournament. Weigh stations are open until 4 p.m. 410-255-5535; www.mssa.net.
Colonial Food and Feasts
See how settlers might have prepared their Thanksgiving dinners in 17th- and 18th-century Virginia. Jamestown Settlement and Yorktown Victory Center, Yorktown, Va. 9 am.-5 p.m. 888-593-4682; www.historyisfun.org.
Made in Mathews Studio Tour
Artists all over Virginia's Mathews County will welcome visitors during this open-studio weekend. Fri.-Sat. 10 a.m.-5 p.m.; Sun. noon-5 p.m. 804-725-4229; www.madeinmathews.net.
Cape Charles Oyster Roast
Fresh, local oysters and other great food, live music and a silent auction round out this annual oyster roast to benefit the town's historical society. Cape Charles Museum, Cape Charles, Va. 5-9 p.m. 757-331-1008; www.capecharles.org.