1 Maryland Renaissance Festival, Crownsville
August 24 - October 20, 2019 (weekends)
Maryland Renaissance Festival re-creates a 16th-century English Tudor village in the era of William Shakespeare and Henry VIII. Renn Fest pays homage to the era with live performances, jousting, and meandering street acts which include a fire-eater, jugglers, magicians and enchanting Renaissance music.
Enjoy a variety of food (must try the turkey leg) and explore a unique world of crafts and artistry featuring glass-blown creations, stained glass, jewelry, pottery, wood-works, leatherwork and clothing.
More about Maryland Renaissance Festival
1821 Crownsville Road
Annapolis, MD 21401
2 Free Fall Baltimore
October 1-31, 2019
Free Fall Baltimore is a citywide arts celebration offering hundreds of free arts and cultural activities at participating venues throughout Baltimore.
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401 W Pratt St
Baltimore, MD 21202
3 The Fall Foliage Experience, Cumberland to Frostburg
October 2019, except Mondays
Climb aboard the restored diesel locomotive on the Western Maryland Scenic Railroad and climb through the beautiful Allegheny Mountains. A narrator on-board provides "color" about the history and cultural locations along the way. Autumnal colors, vintage railroad experience, what could be better in the Fall.
More about Western Maryland Scenic Railroad
13 Canal St
Cumberland, MD 21502
4 Ghost Tours & Haunted Attractions
If you enjoy being creeped-out ... you will love the alleyways of old Annapolis and the frontier graves of Frederick. The Old Line State has spent nearly 400 years collecting her ghosts. Those restless spirits are out there, waiting for YOU.
5 Darlington Apple Festival
October 5, 2019
Darlington Apple Festival is a popular annual one-day event in the quaint village of Darlington, featuring apples, pumpkins, mums, crafts, entertainment, art, country market, refreshments and more!
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2110 Main Street
Darlington, MD 21034
6 Taste of Bethesda
October 5, 2019
Bethesda's famous food and music festival brings 60 restaurants and five stages of entertainment to Bethesda's Woodmont Triangle. Each year, more than 40,000 attendees sample the delicious restaurants, enjoy the live entertainment and visit the kid's corner for face painting and arts & crafts.
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Bethesda, MD 20814
7 52nd Annual Autumn Glory Festival, Oakland
October 9-13, 2019
Travel & Leisure named Oakland America’s Best Town for Fall Colors, and with good reason. Celebrate Mother Nature’s gorgeous foliage surrounding Deep Creek Lake with parades, a farmers market, concerts, antiques and crafts shows, and even a car show!
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Garrett County, Maryland
McHenry, MD 21541
8 Maryland Wine Festival, Westminster
This event at the Carroll County Farm Museum has grown from an informal gathering on a local farm to a hub for local wineries to showcase their products to nearly 25,000 attendees. Enjoy food, music, artisan vendors and winemaking demonstrations. Take an educational seminar and learn the ins and outs of wine tasting. Feeling adventurous? Participate in the Amateur Wine Judging.
More about The Maryland Wine Festival - NEW DATES
500 S Center St
Westminster, MD 21157
9 Catoctin Colorfest, Thurmont
October 12-13, 2019
Local art, jewlery, crafts, and a variety of delicious food are just a few of the fun things you will find at this annual event that began in 1963! Catoctin Colorfest, in Thurmont, is one of the largest outdoor craft shows on the East Coast and is held as the area's leaves are crescendoing in vibrant colors.
See more Fall Festivals in Frederick!
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Thurmont, MD 21788
10 Autumn Wine Festival at Pemberton, Salisbury
October 19-20, 2019
Do you love wine, the great outdoors, delicious food and live entertainment? If so, Autumn Wine Festival at Pemberton Historical Park in Salisbury is for you! Produced in partnership with the Maryland Wineries Association.
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5561 Plantation Ln
Salisbury, MD 21804
11 10K Across the Bay, Annapolis
The Across the Bay 10k is one of the largest, most exciting mid-distance events anywhere. 4.35 miles of the 10K course takes place over water, on the Chesapeake Bay Bridge. The Navy-Marine Corp Stadium is one of several 10K parking lots (additional fee/pre-registration required)
12 Waterfowl Festival, Easton
November 8-10, 2019
A wildlife art and sportmans expo, providing the ultimate experience for sporting and outdoor enthusiasts. Join in the celebration of Maryland's sporting heritage and Eastern Shore food, drink and fun!
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40 South Harrison Street
Easton, MD 21601
13 Chesapeake Bay Fall Classic Rockfish Tournament, Annapolis
Thousands of recreational and professional anglers from Maine to North Carolina will be making their way to Maryland to compete for top honors and a chance at some big money in this year’s Chesapeake Bay Fall Classic, the Bay’s largest fall rockfish tournament. With over 250 boats and 1,500 anglers regularly competing, the prizes and competition is larger than ever.
Sandy Point State Park
14 Amish Quilt Auction, Mechanicsville
November 16, 2019
St. Mary's is proud of its Amish heritage. Be part of the tradition at the annual quilt auction in Mechanicsville. Bid on beautiful Amish-made quilts and other gorgeous hand-stitched items at this traditional Amish Auction. The annual auction features smaller hand-sewn items plus wonderful baked goods and delicious home-made soup.
More about Amish Quilt Auction
Grove Farm Lane
Mechanicsville, MD 20659
15 Thanksgiving Events and Things to Do
Over the river and through the woods… Let's make memories, and perhaps start a new family tradition, at these Thanksgiving oriented events in Maryland.
16 Seafood Festival Season is Here!
Sample seafood all around the state. The 52nd annual U.S. Oyster Festival is in St. Mary’s. Don’t miss the crowning of King Oyster, or the heated competition in the National Oyster Shucking Championships, plus seafood, beer tastings and more. But that’s not all: Oysterfest 13 comes to Baltimore, the Chesapeake Bay Maritime Museum hosts its annual OysterFest in St. Michaels, Tilghman Island Day is just around the corner, and much more! Get all of the info at our Seafood Festivals page.
17 Annapolis Boat Shows
United States Sailboat Show
October 10-14, 2019
Bring the family to this world-famous sailboat show where you will find something for everyone; seminars, clothing & accessories, and boats of all sizes. Enjoy the many shops and restaurants in historic Annapolis.
United States Powerboat Show
October 3-6, 2019
Miles of docks exhibit everything from luxurious motor and ocean-going yachts and “down east” trawlers to high-performance powerboats and offshore fishing machines. On display are boats of every style from 8’ to 80’ including water toys of all types, express cruisers, inflatables, paddle boards, ski boats, trailerable powerboats, pontoons, and an extensive collection of center console fishing boats.