CBMM Boat Auction
You never know what interesting vessels will show up on the auction block at Chesapeake Bay Maritime Museum's annual boat auction, as everything from wooden skiffs to classic sloops are put up for sale. Chesapeake Bay Maritime Museum, St. Michaels, Md. Gates open at 8 a.m.; auction 1 p.m. 410-745-2916; www.cbmm.org.
The Kent Island Yacht Club hosts this annual Kent Island Cup, where outrigger canoes will battle it out in relay races. A luau featuring great food and music will follow Saturday's races. Stevensville, Md. Races start at 7:30 a.m. 410-544-3804; www.kiocc.com.
Aug. 31-Sept. 2
Skipjack Race and Festival
The Deal Island-Chance Lions Club hosts this annual end-of-summer do, featuring skipjack races, a parade, live music, a crab-pot tossing contest, a blessing of the fleet and a fishing tournament. Chance, Md. Sat. 4-10 p.m.; Sun. 1-11:30 p.m.; Mon. 8 a.m.-6:30 p.m. skipjack races 9:30 a.m. 410-784-2799; visitsomerset.com.
Check out a plethora of gorgeous yachts on display Saturday afternoon during an open house at this year's annual Hatteras 1510 Club National rendezvous. Harbor East Marina, Baltimore. www.hatteras1510club.com.
Bay Seafood Festival
This one sold out last year, so buy your tickets early for the 23rd annual all-you-can-eat seafood festival on the banks of the Rappahannock. The festivities also include live entertainment, a raffle and auction, and a free water taxi to bring boaters ashore. Advance ticket purchase required. Belle Isle State Park, Lancaster, Va. 4:30-10 p.m. 800-777-9717; www.kiwsrotary.com.
Mathews Market Days
Mathews County's fall festival will feature an art show, crafts demonstrations, live entertainment, an outdoor dance and more. Village Green, Mathews, Va. 9 a.m.-5 p.m.; street dance Sat. 8-11 p.m. 804-725-7196; mathewsmarketdays.com.
Hampton Bay Days
Celebrate the Bay with lots of live music, an indoor juried art show, arts and crafts vendors, two full-scale carnivals and fireworks. There will also be educational Bay exhibits, workboats and research vessels on display. Downtown Hampton, Va. Fri. noon-11 p.m.; Sat. 10 a.m.-11 p.m.; Sun. Noon-6 p.m. 757-727-4290; www.baydays.com.
Liberty Ship Cruise
Tour the Patapsco River aboard the historic Liberty Ship John W. Brown. There will be historic demonstrations, military fly-bys and re-enactments. Tickets required. North Locust Point Marine Terminal, Baltimore. 10 a.m.-4 p.m. 410-558-0164; www.liberty-ship.com.
National Capital Leukemia Cup Regatta
This annual PHRF and one-design regatta hopes to beat last year's $142,000 total, raised for the Leukemia and Lymphoma Society. Washington Sailing Marina, Alexandria, Va. Call for details. 703-399-2957; www.leukemiacup.org/nca.
Enjoy cocktails, dinner and dancing on Navy Point during Chesapeake Bay Maritime Museum's annual fall gala fundraiser. Chesapeake Bay Maritime Museum, St. Michaels, Md. 5:30-10 p.m. 410-745-2916; www.cbmm.org.
Join Sultana Projects' naturalists for a kayak paddle exploring a quiet creek just outside Chestertown, Md. Kayaks provided. Turner's Creek Public Landing, Chestertown, Md. 10 a.m.-12:30 p.m. 410-778-5954; www.sultanaprojects.org.
Oyster Roast and Dance
Come for the oysters, stay for the music and dance away the evening at this museum fundraiser. Deltaville Maritime Museum, Deltaville, Va. 5-9 p.m. 804-776-7200; www.deltavillemuseum.com.
Boardwalk Arts Show
More than 150 artists' works will be displayed along the boardwalk at Colonial Beach, Va., during this popular annual arts show. Colonial Beach, Va. 10 a.m.-5 p.m. 804-224-8145; www.colonialbeach.org.
Pirate Adventure Weekend
The Maryland Renaissance Festival welcomes pirates of all salty backgrounds during this theme weekend of Maryland's long-standing fall "Ren Fest." Crownsville, Md. 10 a.m.-7 p.m. 800-296-7304; www.rennfest.com.
Maryland Seafood Festival
Sandy Point State Park will transform itself into a showcase for local and regional purveyors of delicious seafood, many of whom will compete in the Capital newspaper's crab soup cook-off (Saturday). There will also be arts and crafts vendors, wine and beer tastings, contests, a kids interactive zone and more. Sandy Point State Park, Annapolis. Fri.-Sat. 10 a.m.-9 p.m.; Sun. 10 a.m.-7 p.m. www.mdseafoodfestival.com.
Alexandria Arts Festival
Browse through six blocks of artwork at this annual open-air festival of the arts. The festival features the work of over 200 artists, plus demonstrations, a children's activity area and food. King Street, Alexandria, Va. Sat. 10 a.m.-7 p.m.; Sun. 8 a.m.-5 p.m. 703-746-3301; www.visitalexandriava.com.
Cruising the ICW
Get expert insight and knowledge from professional captain and cruiser Paul Truelove in this new course focused on the Intracoastal Waterway. Preregistration required. Annapolis School of Seamanship. 9 a.m.-4 p.m. 410-263-8848; www.annapolisschoolofseamanship.com.
Cruises For Kids
Volunteer captains will take seriously ill kids and their families out for a day on the water at Bush River Yacht Club, Abingdon, Md. Register to be a captain yourself or for your family in need at 717-514-6278; www.captainssharingandcaring.org.
Waterfront Wine Tasting
Enjoy a great view of Middle River while enjoying a glass or two of refreshing summer wines. Docking available. Conrad's Ruth Villa, Middle River, Md. 6:30-8:30 p.m. 410-335-4468; www.conradsvilla.com.
Star Spangled Banner Defender's Day Weekend
Fort McHenry's big annual event is a three-day "encampment" and extravaganza featuring War of 1812 re-enactments, visiting ships, concerts and a symbolic naval bombardment, complete with fireworks, to round out the weekend. Fort McHenry, Baltimore. Fri. 5 p.m.-7 p.m.; Sat. 9 a.m.-9 p.m., concert 6:30 p.m., fireworks at dusk. Sun. 9 a.m.-3 p.m. 410-962-4290; www.friendsoffortmchenry.org.
Reedville Antique and Classic Boat Show
This gathering of beautiful old boats comes complete with land and in-water displays, boating vendors, music, food and more. Reedville Fishermen's Museum, Reedville, Va. 10 a.m.-4 p.m. 804-453-3506; www.rfmuseum.org.
Wye Island Regatta
All person-propelled boats (canoes, kayaks, outriggers, etc.) are welcome to compete in this 13.1-mile race around Wye Island. Wye Landing, Wye Mills, Md. 8 a.m.; www.annapolisrowingclub.com.
Music on the Nanticoke
Bring your lawn chairs and enjoy this free waterfront concert by the band Chester River Runoff. Water Street, Vienna, Md. 4-7 p.m. 410-924-7863; www.viennamd.org.
Bid farewell to summer with a block party on Main Street complete with bands, a fun relay race, contests, barbecue, drinks and more. Cambridge, Md. 4-10 p.m. 410-228-1000; www.cambridgemainstreet.com.
Thomas Point Lighthouse Tours
Enjoy a boat ride and a tour of Thomas Point Lighthouse. Space is limited, so book early. Tours depart from the Annapolis Maritime Museum, Annapolis. 9 and 11:30 a.m. 415-362-7255; www.uslhs.org.
Maryland Boatbuilders and Dealers Expo
This in-water and shoreside show will feature custom-built boats from the likes of Judge Yachts, Eastport Yachts and Composite Yachts. There will also be dealers on hand for sportfishers, personal watercraft, boating equipment, electronics, recreational gear, canoes and kayaks and more. Cambridge Yacht Club and Municipal Yacht Basin, Cambridge, Md. www.marylandboatshow.net.
Boatyard Beach Bash
Dig your toes into the sand, dance to great beach music and party the evening away at this annual fundraiser for the Annapolis Maritime Museum, sponsored by the Boatyard Bar & Grill. At the Annapolis Maritime Museum, Annapolis. 5-9 p.m. 410-295-0104; www.amaritime.org.
Washington College's Center for Environment & Society will host this festival, offering river cruises aboard the school's 45-foot research vessel, Callinectes, plus sailing, kayaking, a cardboard boat regatta, pony rides, food, a touch tank for the kids, watershed ecology exhibits and live music. Chestertown, Md. Noon-4 p.m. 410-778-7295; ces.washcoll.edu.
Choptank Heritage Skipjack Race
Head to Cambridge, Md., where you can get up close and personal with Chesapeake Bay skipjacks at the dock (and enjoy shoreside activities), then watch them race along the Choptank River. Cambridge Creek, Cambridge, Md. 10 a.m. 410-228-7141; www.skipjack-nathan.org.
Hampton Roads Sunfish Challenge
Watch as a fleet of 100 tiny sunfish boats sail this 10-mile dinghy race from Willoughby Bay to Old Dominion University's sailing center. 757-285-6017; www.hrsunfishrace.com.
Watershed Awareness Day
Enjoy tours of the historic Bloomfield farmhouse, hayrides, games, food, children's activities and live music at this annual festival to raise funds for the Corsica River Conservancy. Bloomfield Farm, Centreville, Md. Noon-4 p.m. 410-758-0835; www.corsicariverconservancy.org.
Get your fill of all-you-can-eat crabs and barbecue, live music and entertainment at this annual fundraising festival to benefit the Friends of the Rappahannock. Tickets must be purchased in advance. Fairgrounds, Fredericksburg, Va. 4-8 p.m. 540- 373-3448; www.riverfriends.org.
Hospice Cup Regatta
This charity regatta includes PHRF racing, beginner racing in the "Hospice" class, and a festive post-race party. Racing on the Severn River 10 a.m.-3 p.m.; post-race party at Annapolis Sailing School, 3 p.m. 410-919-8393; www.hospicecup.org.
Pirates Pack the Park
Head to the Mariners' Museum, in honor of Talk like a Pirate Day, to help salty folks attempt to break the world record for the largest gathering of pirates (current record: 14,231). In the evening, join in the pirate gala, which will include food, drinks, live music and more. Mariners' Museum, Newport News, Va. 10 a.m.-5 p.m. 757-596-2222; www.mariner.org.
Keels & Wheels
Head over to Annapolis Yacht Club for this annual vintage performance car and boat show, with this year's special emphasis on British Marques. The event is open to the public and will feature DJ entertainment, food, awards and family-friendly fun. Annapolis Yacht Club, Annapolis. 301-996-8919; www.annapolisyc.com.
Lighted Boat Parade
Oxford, Md., isn't waiting around for the chilly December weather for its lighted boat parade. This early season Patriots will delight all those along the creek. Oxford, Md. Dusk. www.portofoxford.com.
St. Mary's Riverfest
This free festival in historic St. Mary's City, Md., will have visiting tall ships, live music, a wade-in with Bernie Fowler, a paddle-in, exhibits, crafts vendors, food, drinks and plenty of fun for the whole family. St. Mary's City, Md. 10 a.m.-4 p.m. (wade-in at 3 p.m.) 301-737-2903; www.stmaryscity.org.
Maryland Lighthouse Challenge
Lighthouse fans from near and far are invited to try visiting 10 participating Bay lighthouses (plus three bonus lights) in a single weekend. Each lighthouse will offer souvenirs, and those who visit all 10 will get a special prize. Sat.-Sun. Lighthouses open 8 a.m.-6 p.m. 410-437-0741; www.cheslights.org.
Stroll along High Street during this annual arts showcase to get a glimpse of local artists' creations. There will also be food, children's activities and skipjack rides. High Street, Cambridge, Md. Noon-5 p.m. 410-228-7782; www.dorchesterarts.org.
Enthusiasts can get their fill of trawler talk in seminars, clinics, entertainment, and of course there will be both new and used trawlers for sale at this annual show. Baltimore Marine Center Harbor View; seminars aboard liberty ship John W. Brown. Baltimore. 8 a.m.-8 p.m. 888-487-2953; www.passagemaker.com.
Celebrate Virginia's Guinea Neck maritime heritage with crafts vendors, entertainment, crab pot- and anchor-tossing contests and fireworks. Abingdon Ruritan Fairgrounds, Bena, Va. Fri. 3-10 p.m.; Sat. 9 a.m.-9 p.m. 804-815-5654; www.guineajubilee.com.
Seven Seas Gam
This Seven Seas Cruising Association event kicks off with a Friday night cocktail party, followed by a day full of seminars and demonstrations by notable speakers (this year's headliner is world-renowned cruiser Beth Leonard). There will also be a flea market, a dinghy raft-up and Saturday night party. Camp Letts, Edgewater, Md. Register online at ssca.org.
Neptune Festival Boardwalk Weekend
This weekend of fun events all along the Virginia Beach boardwalk is the culmination of the month-long Neptune Festival. It will include concerts, arts and crafts, fireworks and much more. Virginia Beach, Va. 757-498-0215, www.neptunefestival.com.
War of 1812 Fair and Reenactment
American and "British" reenactors will recreate the 1814 battle of St. Leonard Creek, while on land, visitors can learn about military life of that period and enjoy craft demonstrations and hands-on activities. Jefferson Patterson Park and Museum, St. Leonard, Md. 10 a.m.-5 p.m. 410-586-8501; www.jefpat.org.
Run What You Brung Regatta
Timed with the harvest moon to ensure great night sailing, this annual around-Kent-Island regatta will end with a party featuring live music. Preregistration required. Mears Point Marina, Kent Narrows, Md. Race begins at 9:30 a.m. 410-739-1000; www.kentislandsailing.org.
Maritime Museum Crab Feast
Help raise money for the Havre de Grace Maritime Museum during this annual all-you-can-eat crab feast. Elks Club, Havre de Grace, Md. 6-9 p.m. 410-939-4800; www.hdgmaritimemuseum.org.
Groovin' in the Park
After a farmer's market in the morning (9 a.m.-1 p.m.), break out your lawn chairs and spend the evening relaxing or dancing to live music on the waterfront. Deltaville Maritime Museum Deltaville, Va. 6-8 p.m. 804-776-7200; www.deltavilleva.com.
The Rappahannock River Yacht Club will host these historic yachts, affectionately called the "world's littlest yacht," for two days of racing and fun on Carter Creek. Rappahannock Yacht Club, Irvington, Va. www.typhoonnationals.blogspot.com.
Poquoson Workboat Races
Watermen will fire up their diesels on Back River to compete for the coveted "King of the Bay" title. On land, spectators can enjoy shoreside activities like a USCG search and rescue demonstration, food and children's activities. Messick Point, Poquoson, Va. 1 p.m. 757-810-4098; www.poquosonseafoodfestival.com.
For more events around the Chesapeake Bay, visit the Cruiser's Calendar at ChesapeakeBoating.net.