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2022 festivals

These are the most popular annual events around the Chesapeake Bay. If we missed anything, please let us know at editor@chesapeakeliving.com

March

Annapolis St Patrick's Day Parade

St. Patrick’s Festival in Annapolis

Annapolis looks like an Irish waterfront village and parties like it too. The first weekend of March starts with an Irish Hooley (party) Saturday on the Annapolis waterfront (advanced tickets required), followed by the Sunday 1pm St. Paddy’s Day Parade down West Street and Main Street, ending with Shamrock the Dock 3-7pm at the Annapolis waterfront.

First weekend of March

Annapolis St Patrick's Day Parade

St. Michaels Chocolate Fest

The Chocolate Crawl goes throughout the town of St. Michaels at participating businesses and restaurants. Chocolate lovers will enjoy shopping throughout town sampling amazing artisan chocolates, desserts, locally crafted wine, beer, and spirits. Each venue will have Chocolate Inspired Tastings for one-to-three tickets. Tickets cost $1 each. This sold out in 2022 before the event. 

First Saturday of March

Annapolis St Patrick's Day Parade

Thurmont Maple Syrup Festival

2022 was 50th anniversary of the Maple Syrup Festival. Cunningham Falls State Park and Gambrill State Park staff demonstrate the traditional way of simmering sap to syrup starting every half hour from 10 a.m. to 2 p.m. each day. Maryland-made maple syrup will be available for purchase, along with light fare and hot beverages at the Nature Center. A $3 donation per person is requested to support the parks.

Second weekend of March

Annapolis St Patrick's Day Parade

Annapolis Film Festival

The Annapolis Film Festival features more than 100 films being shown at venues all over town, along with panel discussions and coffee talks. This film festival is known for its short films from over 35 countries. After a couple of years of showing the films virtually, movie-goers get to get together again in front of the big screen. Check the “Safe Festival” page for updates before going.

Second weekend of March

APRIL

Annapolis St Patrick's Day Parade

St. Michaels Sea Glass Festival

The 10th Annual Eastern Shore Sea Glass and Coastal Arts Festival will be held Saturday, 10am – 5pm and Sunday, 10am – 4pm at the Chesapeake Bay Maritime Museum in St. Michaels, Maryland. It features artisans from around the country featuring coastal and sea-glass-related jewelry, home décor, art, and more. Tickets required.

First weekend of April

Annapolis Boat Show 2021

Bay Bridge Show on Kent Island

The Bay Bridge Boat Show features powerboats of all sizes and makes, as well as the latest in marine gear, accessories, and apparel. Also, the latest fishing gear and boating-related demonstrations. It’s on the banks of the Chesapeake Bay next to the Bay Bridge.

April 21-24

Annapolis Boat Show 2021

Spring SailBoat Show 

The Annapolis Spring Sailboat Show rings in the new season by bringing together sailing enthusiasts from around the Mid-Atlantic. Every April, guests experience an in-water show boasting the sailing industry’s latest boats, gear, and tech. Comparing side-by-side and talking with industry leaders enables all buyers to have the opportunity to easily and efficiently purchase their next new vessel.

April 29 – May 1

MAY

The Lynx, a historic tall ship

Annapolis Up Rigging Maritime Festival

This is a new festival in Annapolis with “Tall Ships,” music, demonstrations, nautical art and lots of food. It starts Friday when historic boats from thorughout the Chesapeake Bay sail in and dock at City Dock. The festival continues through Sunday, with bands playig at the end of each day. 

May 13 – 15

Annapolis Boat Show 2021

U.S. Naval Academy Commissioning Week

Commissioning Week is a celebration of this year’s Naval Academy grads and it’s a weeklong party for everyone, not just Middies. The academy plans a series of events that the public can attend. A popular event for Annapolis residents is the Blue Angles Flight Demonstration on that Wednesday. Boats fill the harbor and people line the water to watch those blue planes streak by.

May 21 – 28

Tea Party reenactment in Chestertown, MD

Chestertown Tea Party Festival

In response to the British Parliament’s closing of the port of Boston, the citizens of Chestertown, Maryland met in May of 1774 and set forth “Resolves” forbidding importing, selling, or consuming tea in Chestertown. The annual reenactment of tossing The Tea Overboard is the centerpiece of the playful Chestertown Tea Party Festival. Colonial artisan vendors, music, children’s activities, Sunday’s beet & wine tasting & the fabulous raft race.

May 27 – 29

JUNE

Tea Party reenactment in Chestertown, MD

St. Michaels Brew Fest

The Brew Fest in St. Michaels features over 100 beers including one-offs, seasonal, collaborations, and casks from local, regional national breweries. Various venues in St. Michaels. Tickets are required, but you can buy them in advance to ensure you can participate.

June 4

Havre de Grace Lighthouse

Havre de Grace Jazz & Blues Fest

Havre de Grace hosts three days of jazz and blue at venues throughout town. 2022 features women of jazz & blues, legendary artists, and Maryland’s rising stars. 

June 3 – 5

Tea Party reenactment in Chestertown, MD

Antique & Classic Boat Festival in St. Michaels

Wooden classics, vintage race boats, and other antique and Chesapeake Bay-related boats come to the Chesapeake Bay Maritime Museum for the annual Antique & Classic Boat Festival and The Arts at Navy Point in St. Michaels, Md. Hosted by the Chesapeake Bay Chapter of the Antique & Classic Boat Society (ACBS), this Father’s Day weekend event brings an era of by-gone days.

June 17 – 19

JULY

Tea Party reenactment in Chestertown, MD

Independence Day!

Small towns all around the Chesapeake Bay have festivals. Some of the bigger ones:

July 4

 

antique farm tractors

Tuckahoe Annual Steam & Gas Engine Show Near Easton

The Tuckahoe Steam and Gas Association has a 70-acre facility five miles north of Easton where they collect, restore, display, and operate a wide variety of vintage industrial machinery and agricultural equipment. Volunteers dress in era costumes to explain and show how the engines work. There is an admission fee. Arrive early. The line of cars builds up early to get in.

July 7 – 10

August

Chesapeake Bay Balloon Festival

Chesapeake Bay Balloon Festival

There are activities for the whole family including the morning ascension balloon lift, hot air balloon rides, tethered balloon rides, balloon glow, live music as well as a DJ, bounce houses, games, food trucks, a mechanical bull, a large variety of vendors, and adult beverages (specifically wine and beer).

August 5 – 7

Rock Hall pirates weekend

Rock Hall Pirates & Wenches Festival

The Pirates & Wenches Festival is the annual pirate invasion of the Chesapeake Bay. It’s a family-friendly event with music, mayhem, and merriment for three days. No admission fee. Everyone dresses in pirate costumes, especially the adults.

August 12 – 14

Chesapeake Bay blue crab

Seafood Fest in Cambridge

All you can eat Chesapeake Bay seafood from 1pm-6pm at Sailwinds Park, 200 Byrn Street, Cambridge. Admission charge. More details TBA.

August 13

Boat docking contest

Watermen’s Appreciation Day

Watermen’s Appreciation Day celebrates Chesapeake watermen and their heritage. The event includes a “watermen’s rodeo” boat docking contest, and live music. Steamed crabs, beer, and other foods and beverages will be available for purchase.

August 14

Taylor Island boat docking

Taylors Island Boat Docking Challenge

The Taylors Island Boat Docking Challenge is an annual fundraising event benefiting the Taylors Island Volunteer Fire Company. It features the very best watermen and boat dockers on the Chesapeake Bay. The event is generally now held on the Sunday prior to the Labor Day weekend. This is a remarkable and fun event that you don’t want to miss!

Sunday before Labor Day – August 28

September

Rock Hall Village in Rock Hall, Maryland

Scrapple Festival in Rock Hall

Do not tell us that you’ve not been to a Scrapple Festival. This is your chance to correct that. It’s at the Rock Hall Volunteer Fire Department. What is scrapple? A rural Maryland breakfast treat of pork, or other meats, stewed with cornmeal and shaped into loaves, which are then sliced and fried. 

September 3

The Concord Lighthouse in Havre de Grace

Havre de Grace Waterfront Festival

At Concord Point Park and the Moore Family Homestead, you can enjoy steamed crabs, seafood, live bands, food trucks, beer gardens, vendors, entertainers, artisans, games, contests, exhibits, crafts, kid zones, land & water demonstrations, youth fishing derby, pony rides, live mermaids, hot air balloons.

September 9 – 10

Susquehanna Wine & Seafood Festival

Susquehanna Wine & Seafood Festival

The festival will feature 20+ local restaurants and food trucks. Each restaurant will serve signature seafood dishes ranging from crab cakes, lobster rolls, grilled oysters, and fish tacos as well as Maryland steamed crabs (of course)! There will also be non-seafood fare available. The festival also features 60+ wines, signature cocktails, and brews, as well as live music, cooking demos by local chefs, wine pairings, mixology demonstrations, unique shopping, a VIP tent, and a family zone.

September 24

Maryland Seafood Festival

Maryland Seafood Festival

This is a huge annual event at Sandy Point State Park in Annapolis. The Maryland Seafood Festival hosts loads of seafood vendors, local shopping and vendor options, a fantastic beverage selection with lots of local craft beer and tons of kids activities, all hosted along the beautiful shores of the scenic Chesapeake Bay.

September 24

Susquehanna Wine & Seafood Festival

Susquehanna Wine & Seafood Festival

The festival will feature 20+ local restaurants and food trucks. Each restaurant will serve signature seafood dishes ranging from crab cakes, lobster rolls, grilled oysters, and fish tacos as well as Maryland steamed crabs (of course)! There will also be non-seafood fare available. The festival also features 60+ wines, signature cocktails, and brews, as well as live music, and cooking demos by local chefs.

September 24

Mid Atlantic Small Boat Festival

Mid-Atlantic Small Craft Festival

Hundreds of amateur and professional boat builders, model boat builders, and enthusiasts come from all over the region to display their skiffs, kayaks, and canoes. Watch many of these one-of-a-kind vessels race along the Miles River.

September 24

October

oyster shucking

Rock Hall Fall Festival

This is all about the oysters. As you eat oysters, musicians hold forth throughout the day, oysters are local and plentiful, and children can participate in captivating and free activities. Approximately 40 handicraft vendors show and sell their wares at the festival and a large selection of food vendors serve up regional favorites.

 

Oct. 8? (date to be confirmed)

U.S. National Oyster Shucking Competition

U.S. Oyster Festival in Leonardtown

Oysters, bands, a shucking contest, and a cook-off. This is where the National U.S. Oyster Shucking Championship takes place. The festival takes place at the St. Mary’s county fairgrounds. It’s that big.

Third Weekend in October (Oct. 15-16)

Chesapeake Bay oyster

OysterFest in St. Michaels

This festival features live music on two stages, boat rides, retriever demonstrations, oysters and other local fares, an oyster stew competition and cooking demonstrations, along with children’s activities, oyster demonstrations, and harvesting displays. This Maritime Museum event sells out, but oyster shuckers will be set up on the streets in St. Michaels. There is plenty of opportunity for buck-a-shuck oysters. 

October 29

November

Easton Waterfowl Festival

Waterfowl Festival in Easton

The annual Waterfowl Festival is huge, a wildlife art show, sportsman’s expo, and small-town festival celebrating all things “Eastern Shore” and showcases Easton in its autumn glory. Meet the country’s finest wildlife artists: painters, sculptors, carvers, and photographers, and see their work in galleries spread across historic downtown Easton.

 

November 11 – 13

Annapolis St Patrick's Day Parade

St. Michaels Sea Glass Festival

The 10th Annual Eastern Shore Sea Glass and Coastal Arts Festival will be held Saturday, 10am – 5pm and Sunday, 10am – 4pm at the Chesapeake Bay Maritime Museum in St. Michaels, Maryland. It features artisans from around the country featuring coastal and sea-glass-related jewelry, home décor, art, and more. Tickets required.

November 19-20

December

Maryland Avenue in Annapolis during Christmas Midnight Madness

Annapolis Midnight Madness

Annapolis shops stay open late and the town brings musicians into town to walk about and entertain shoppers as they explore all the shopping in the historic district. Each street hosts a different holiday look.  

First 3 Thursdays of December

Arrow Series bowl from Hegland Glass

Chestertown Art Walk

National-level artists open their studios to the general public during the Chestertown Art Walk. Dozens of artists and artisans will be selling works at galleries, storefronts, restaurants, and around town. Live music will also be happening throughout town.

December 17