6 Can’t-Miss Fall Festivals in Annapolis for 2018 ?

What’s arguably the best time of year in Annapolis is almost upon us: In the fall, and the summer-to-fall transition period, Annapolis becomes a hub for fairs and festivals. From day-long events to weekend fests that last all season long, an abundance of beer, wine, seafood, cultural celebration and even 16th-century time travelers make their presence known about town this time of year, and we couldn’t be more excited. Here are six big festivals hitting Annapolis in the 2018 season. 

The Maryland Renaissance Festival

Aug. 25 – Oct. 21

Celebrating its 42nd season, the Maryland Renaissance Festival in Crownsville spans nine weekends from late August to October, all filled with vendors and crafts, jousts, elaborate storylines and unlimited entertainment of the 16th century variety. 

Such entertainment includes 20-minute plays by Shakespeare’s Skum, a performance group now in its 34th year; A Fool Named “O,” the mime; a wide variety of renaissance comedy, musical, juggling and knife-swallowing acts from across the country; and, of course, King Henry VII and his Royal Court, who wander the village daily with all the pomp and circumstance you’d expect from such a crowd.

Dawn your own tudor-style dresses and waist cinchers, or rent costumes on site. Just be sure to leave some extra room in your corsets or breeches for the inevitable turkey leg and pork pocket-feasting. 

Maryland Seafood Festival

Sept. 8

Mark your calendar for the ultimate Maryland foodie event, the annual Seafood Festival. The Maryland Seafood Festival is now in its 51st year and will take place at Sandy Point State Park, where assorted seafood dishes, cooking demonstrations, competitions, kids’ activities and more will keep seafood connoisseurs of all ages occupied all day.

Not only is the Seafood Fest an opportune moment for feasting on oysters and crab soup, but it also makes for a fun way to give back to the community. A portion of the festival’s proceeds will be donated to local charities, and a number of non-profit organizations will be present at the festival’s Chesapeake Arts Village. 

Attendees can expect live music all day long, soup tasting for the Crab Soup Cook-Off, eating, picking and shucking contests, arts and crafts vendors, a sandy soccer game for registered teams, an Entertainment Ave. packed with kid-friendly activities, and, of course, plenty of food. 

Kunta Kinte Heritage Festival

Sept. 29

For 29 years, the Kunta Kinte Festival has celebrated the perseverance, education, and cultural heritage of Africans, African Americans and Caribbean people of African descent. Named after one of 98 slaves brought to Annapolis on the Lord Ligonier ship in 1767, Kunta Kinte remained in touch with his heritage while in America and is a symbol of the struggle all ethnic groups face to preserve their cultural heritage. 

Festival-goers will find all kinds of entertainment ranging from music to dance to a speaker performing as Frederick Douglas. Vendors will be on-site with arts and crafts, educational tools and information, and food, and the “Young Entrepreneur” application allows enterprising youth aged 7 – 16 to have an arts and crafts booth at the festival for a significantly reduced fee. 

Twist & Stout Beer and Wine Festival

Sept. 29

Set upon the picturesque backdrop of Quiet Waters Park, Twist & Stout will feature fine wine and craft beer, in addition to live music, food trucks, and plein air artists creating works on-site. Hosted by the Anne Arundel County Department of Parks and Recreation in partnership with the Maryland Wineries Association, tickets include unlimited tastings from Maryland’s finest craft breweries and wineries, and benefit the Quiet Waters Park Nature Center Campaign to promote environmental education, advocacy, and stewardship.

The event is expected to draw around 4,500 people, who will all be able to enjoy the “crown jewel” of the county’s parks system while listening to live music and enjoying delicious local libations. 

Annapolis Harvest Beer Festival

Oct. 14

Beer lovers who aren’t able to make the Twist & Stout fest, fear now: the Annapolis Harvest Beer Festival was made just for you! This festival celebrates the season with Maryland’s best harvest beers, right in the heart of the city on West Street. Organized by the Chesapeake Brew Pub of Annapolis, this beer festival will feature new area breweries Chesapiioc, Crooked Crab and Checkerspot, plus long-time favorites like Jailbreak and Gypsy Brewing Company.  

Eight breweries in total will on festival grounds pouring their best pumpkin lagers and seasonal stouts, and guests can also expect to enjoy a homebrewing contest with celebrity judges, live entertainment, pumpkin carving, demos and food. 

For those who aren’t to make Annapolis Harvest, Shore Craft Beer’s OCtoberfest festival will take place in Ocean City just two weeks later. 

Oyster Festival

Oct. 21

Whether you like your oysters raw, fried or cooked in a soup, there’s something for everyone at the annual Oyster Festival (at least, if you like oysters, but hotdogs, hamburgers and desserts will be available, too). Hosted by the Captain Avery Museum in Shady Side, the 1859 historic waterman’s home-turned-museum has been holding the event now for 16 years. 

The Oyster Festival will additionally feature live music by Bob & Eddie, the Eastman String Band and Hat Trix and children’s activities that include live crab races, face painting, balloon sculptures, crab toss, a live touch tank, sand art and pirate photos.