Top Maryland Events and Festivals

Plan a trip around one of these events and festivals which are as diverse as Maryland itself.

By Heather Cisar

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Kunta Kinte Heritage Festival
Kunta Kinte Heritage Festival
Image Credit: DelFest

To see some unique artistry—and occasional downright quirkiness—check out these annual events held across the state. From ice extravaganzas to celebrations of music and art, to an event all about marshmallow Peeps, Maryland’s event calendar is filled with fun.

A flight of beer from Evolution Craft Brewing Company Image Credit: Wicomico County Tourism

FeBREWary in Maryland, Statewide - February

FeBREWary is Maryland’s official month-long celebration of craft beer, and with craft brew events on tap across the state.  From the mountains to the beach, FeBREWary in Maryland is the perfect opportunity to hoist a pint with good friends in great places.  
More info...FeBREWary in Maryland

PEEPShow Carroll Arts Center Westminster Image Credit: Carroll County Arts Council

PEEPShow, Westminster - March/April VIRTUAL Pre-Show for 2020

Peeps aren’t just for eating, and this event proves it. Each spring at the Carroll Arts Center in downtown Westminster, spectators vote for their favorites among hundreds of marshmallow masterpieces, including sculptures, dioramas, mosaics and videos. Don’t forget to bring your sweet tooth!

For 2020, PEEPShow was reconceived as an on-line event for the first time.


More about PEEPshow 2020 - An On-Line Prequel Show


Type:
Events


Location:
91 West Main St
Westminster, MD 21157
410-848-7272


Learn More
Annapolis Arts and Crafts Festival

Annapolis Arts Week - VIRTUAL - June 2020

First Sunday Arts Festival typically takes place on the first block of West Street in downtown Annapolis the first Sunday of the month from May through November. This year, it’s gone virtual for the entire month of June.

First Sunday Arts Festival has been converted into a month-long Virtual Arts Festival. Listen to music, order food, win prizes and shop over 200 artists online.

U.S. Air Force Air Demonstration Squadron "Thunderbirds" fly over Ocean City Image Credit: DVIDS/USAF/Master Sgt Stan Parker

OC Air Show, Ocean City - August 15-16, 2020

The annual OC Air Show features either the USN Blue Angels or the USAF Thunderbirds! The OC Air Show keeps getting bigger and better thanks to the hundreds of thousands of spectators who come out to make it a success!.


More about OC Air Show


Type:
Events


Location:
Ocean City Beach Area
Ocean City, MD 21842
410-289-2800


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Historic National Road

Historic National Road Yard Sale Days, Route 40 - August 19 - 23, 2020

How many of the 824 miles of yard sales can you handle? Each area offers its own treasures, food specialities and charm. Historic National Road Yard Sale is one of the greats and it begins in Western Maryland on and near Historic Route 40.

Usually scheduled for May or June, this beloved event has moved to August 2020.


More about Historic National Road Yard Sale Baltimore to St Louis


Type:
Events


Location:
151 S. East St.
Frederick, MD 21701
765-987-7565


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Ocean City is the White Marlin Capital of the World.

White Marlin Open, Ocean City - August 3-7, 2020

This renowned Annual White Marlin Open is the world's largest billfish tournament. Over 300 boats vie for well over $4 million in prize money. Registration fees for participating boats.


More about White Marlin Open


Type:
Events


Location:
Harbour Island Marina
Ocean City, MD 21842
410-289-9229


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See the Blue Angels fly during Fleet Week in Maryland

Maryland Fleet Week Baltimore - VIRTUAL - September 8-11, 2020

Fleet Week offers exciting experiences—as U.S. Navy vessels will be ready for boarding, this time VIRTUALLY. Commemorating history while showcasing state-of-the-art technology, military service branches will present a family-friendly virtual festival. More info...

Image Credit: Charm CityJunction

Berlin's Fiddlers Convention - September 25-27, 2020

Fiddling and blue grass music fills the street. Food and craft vendors, beer garden and games for the children.


More about Berlin Fiddler's Convention


Type:
Events


Location:
Downtown Berlin
Berlin, MD 21811
410-641-4775


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Preakness AP Finish Image Credit: Jim McCue

Preakness Stakes, Baltimore - October 3, 2020

The Preakness is one of the nation’s largest, single-day, annual sporting events! Baltimore's Old Hilltop comes alive with the running of the Preakness Stakes, where the finest three-year old thoroughbreds compete.

Always in May, this year's Preakness moved to October 3, 2020.  Look for the Preakness to return to May next year.

Cyclists at the Six Pillars Century Blackwater Tour Image Credit: visitdorchester.org

Six Pillars Century Blackwater Tour, Cambridge - October 10, 2020

This event at Great Marsh Park in Cambridge offers courses tailored for fun, fitness and endurance, ranging from the 11-mile Family Ride to the 56-mile Ironman Eagleman course and 100-mile Century Course. Cycle through the Blackwater National Wildlife Refuge, named one of the "Last Great Places" by the Nature Conservancy. Start with a complimentary al fresco breakfast, bike the scenic paths, then finish off a great day with a picnic in the park.  Check the 2020 Six Pillars Century Blackwater Tour for updates.

J Millard Tawes Crab and Clam Bake Image Credit: Somerset County Tourism

J. Millard Tawes Crab and Clam Bake, Crisfield - October 14, 2020

All you can eat seafood, side dishes, beer and soda. A Maryland must attend - see and be seen annual event named after Crisfield native, J. Millard Tawes, 54th Maryland Governor. Traditionally held every July, the 2020 J. Millard Tawes Crab and Clam Bake is held on October 14.


More about J. Millard Tawes Crab and Clam Bake - New Date!


Type:
Events


Location:
715 Broadway
Crisfield, MD 21817
410-968-2500


Learn More
Sunfest in Ocean City

Ocean City Sunfest - October 1-4, 2020

Summer lasts longer in Ocean City! Enjoy four days of family fun, arts, crafts, live music and food. Admission is free except for ticketed performances.


More about Ocean City Sunfest


Type:
Events


Location:
809 S. Atlantic Ave
Ocean City, MD 21842
410-289-2800


Learn More
This festival held over 4 days in fall has tons of family-friendly things to do.

Autumn Glory Festival, McHenry - October 7-11, 2020

Celebrate amazing Fall Foliage with two large parades, concerts, band competitions, art exhibits, fall foliage tours, craft shows and more. This annual five-day celebration of autumn takes place in the western Maryland that boasts incredible scenery and nature. .


More about Autumn Glory Festival


Type:
Events


Location:
Garrett County
Deep Creek Lake, MD 21541
888-387-5237


Learn More
Baltimore Book Festival Logo Image Credit: BOPA

Baltimore Book Festival - Brilliant Baltimore - Fall 2020 - Dates TBD

The Baltimore Book Festival will alternate every year with Light City to create Brilliant Baltimore, a one-of-a-kind event on Baltimore’s waterfront. The Book Festival is a celebration of the literary arts, and features author appearances, book signings, readings, children’s activities, and more. Plans are being put in place, so please contact the Baltimore Office of Promotion and the Arts for details.

ICE Gaylord Holiday Extravaganza

ICE! - National Harbor - November/December

Embrace the delights of winter at this seasonal ice sculpture show at the Gaylord National Resort & Convention Center in National Harbor. Don't worry, full-length snow coats and blankets are provided to keep you warm and cozy while you marvel at the sculptures. The theme of this popular annual event changes every year, but you can count on seeing beloved children’s characters and staples like an ice slide. 

Kwanzaa Celebration featuring Sankofa Dancers Image Credit: Courtesy of Reginald F. Lewis Museum

Kwanzaa Celebration, Baltimore - December/January

Kwanzaa is celebrated in the United States for seven days, starting December 26 and ending on January 1.  The Reginald F. Lewis Museum of Maryland African American History and Culture offers a series of Kwanzaa programs including storytelling, crafts and traditional performances.

Black-eyed Susans in a Garden Image Credit: 813photography-instagram

Secret Garden Tour of Havre de Grace - May 2021

Tour the lovely private gardens of historic Havre de Grace. Start at the Havre de Grace Maritime Museum for your ticket and map.  Then meander along the Susquehanna River on this self-guided tour that features fabulous gardes. Stop by the Garden Mart and Plant Sale for native plants and the food vendors for a bite to eat. There are nature-inspired presentations and demonstrations, too, for those with green thumbs looking for inspiration for their own gardens. 

Image Credit: Brad Kuntz

DelFest, Cumberland - May 2021

Memorial Day Weekend means Bluegrass at this festival at Allegany County Fairgrounds. Featuring the Del McCoury Band and a stellar list of musicians who excel at this style of music. You're in for five days of festive fun at this top event.

A Conducting Class at the National Music Festival in Chestertown

National Music Festival, Chestertown - June 2021

Two Weeks of Orchestral Concerts - soloists, chamber, full orchestra - plus hundreds of open free rehearsals. Affordable, adventurous performances. Reservations recommended.

The Antique and Classic Boat Festival in St. Michaels is a summertime celebration of all things nautical. Image Credit: www.cbmm.org

Antique and Classic Boat Festival, St. Michaels - June 2021

This festival is a real crowd pleaser no matter what age you are. Hundreds of architecturally exquisite wooden classics, vintage race boats and more are on display on the land and in the water at St. Michaels in June. Festivities include live music, boat rides, food and family activities. 

Artscape Arts Festival Painting

Artscape, Baltimore - Returning July 2021

America's largest free arts festival, attracting 350,000+ attendees over three days. Features 150+ fine artists, fashion designers and craftspeople; visual art exhibits on and off-site, outdoor sculpture, art cars, photography; live music and more.
 

Little Yough Summer Music Festival, Oakland - Returns July/August 2021

Free Friday night concerts at the Mountain Fresh Pavilion in Oakland. Back with a new line-up for the new season of this popular series.
More info...

Country Fest and Auction in McHenry Image Credit: https://www.facebook.com/countryfestandauction

Country Fest and Auction, McHenry - Returns August 2021

Held at the Garrett County Fairgrounds in McHenry, this August event combines history, fine art and tasty Maryland BBQ. Check out the auction items like authentic quilts, crafts and Amish-made furniture, and let the kids take a ride on a pony or “barrel of fun,” and pedal tractor pulls. Everyone will enjoy the hay rides, miniature horse and cart rides, and the petting zoo—plus free admission and parking.  

People Gathered at the Watermen's Appreciation Day Festival Image Credit: Chesapeake Bay Maritime Museum

Watermen’s Appreciation Day, St. Michaels - August 2021

This August celebration ranks high on the list of fun summer things to do, and includes a “watermen’s rodeo” boat docking contest, boat rides, live music, kids’ activities, and—of course—fantastic seafood.  

Vegan SoulFest Logo Image Credit: Vegan SoulFest

Vegan SoulFest, Baltimore - August 2021

Vegan Soulfest is a celebration of culture and veganism. All vegan. All soul. 7th annual. New artists, speakers and cooking exhibitionists.

Kunta Kinte Heritage Festival

Kunta Kinte Heritage Festival, Annapolis - September 2021

The Kunta Kinte Heritage Festival is a free, family-friendly celebration of the perseverance, education, and cultural heritage of Africans, African Americans, and Caribbean people of African descent.The festival features a full day of live music, dance performances, and vendors!

People at the National Folk Festival Image Credit: Courtesy of NCTA/Photo Credit: Edwin Remsberg

National Folk Festival, Salisbury - September 2021

Experience the oldest multi-cultural traditional arts celebration in the United States.  This is a three day outdoor festival that is free to the public.  Expect to see and hear some of the best talent from throughout North America.

The extremely popular National Folk Festival returns in September 2021.

Featured Places
PEEPshow logo
01
Location:
91 West Main St
Westminster, MD 21157
U.S Air Force Thunderbirds
02
Location:
Ocean City Beach Area
Ocean City, MD 21842
yard sale flyer
03
Location:
151 S. East St.
Frederick, MD 21701
White Marlin Open logo
04
Location:
Harbour Island Marina
Ocean City, MD 21842
People at the Fiddlers Convention in Berlin
05
Location:
Downtown Berlin
Berlin, MD 21811
Baskets of steamed crabs
08
Location:
715 Broadway
Crisfield, MD 21817
Sunfest Logo
09
Location:
809 S. Atlantic Ave
Ocean City, MD 21842
Fall Foliage in Garrett County, Maryland
10
Location:
Garrett County
Deep Creek Lake, MD 21541
Browse Featured Places

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