The Most Epic Annual Events in Maryland: Top 10 Must-Experience Festivals (Currently Open)
Maryland does festivals like it does blue crabs—bold, plentiful, and full of flavor. From coastal spectacles on the Chesapeake Bay to art-soaked city streets in Baltimore, to heritage celebrations on the Eastern Shore, the Old Line State throws world-class events all year long. This curated guide spotlights the top 10 annual festivals in Maryland that are currently operating, wildly beloved, and worth planning a trip around. You’ll find can’t-miss highlights, insider tips, family-friendly notes, and the kind of details that turn a good outing into an unforgettable tradition.
Whether you’re a curious tourist, a weekend-seeking local, or a family plotting a memory-packed getaway, these are the festivals that define Maryland culture—iconic, immersive, and evergreen.
Maryland Renaissance Festival (Crownsville): A Storybook State of Mind
What it is: For late-summer through mid-fall, a wooded village called Revel Grove becomes Maryland’s grand stage for knights, minstrels, jousts, and turkey legs bigger than your forearm. The Maryland Renaissance Festival is one of the largest and longest-running “Ren Faires” in the country, with full-day programming, costumed performers, artisan wares, and themed weekends that make repeat visits irresistible. Maryland Renaissance Festival+2Maryland Renaissance Festival+2
Why it’s epic
Massive cast of performers and roving characters that pull you straight into the story.
Tournament-style jousting, musical stages, and comedy acts for all ages.
A marketplace stacked with hand-crafted leather, blades, jewelry, and period garb—true craft culture.
Signature experiences
Joust & royal court shows (arrive early for best vantage).
Hearty festival fare—from sausage-on-a-stick to hand-pies and (yes) the mythical turkey leg.
Dress-up culture: casual cosplay welcome—kids love it, and adults do, too.
Pro tips
Weekends are busiest; arrive early and pre-purchase tickets when available.
Expect a fair amount of walking on natural pathways; comfortable footwear is essential.
Preakness Stakes Week & Infield Experiences (Baltimore): Maryland’s Party at the Track
What it is: The Preakness Stakes, the storied second jewel of horse racing’s Triple Crown, transforms Pimlico Race Course and Baltimore at large into a weeklong celebration of speed, music, fashion, and Maryland pride. Expect race-day traditions (the Black-Eyed Susan is more than a flower), star-powered concerts, and a fan atmosphere unlike any other in the mid-Atlantic. Visit Baltimore+2WBAL+2
Why it’s epic
Nationally significant sporting event with deep Maryland roots.
Festival programming beyond the track: concerts, community events, and themed festivities across the city.
A dress-to-impress moment—statement hats encouraged.
Signature experiences
Race day at Pimlico with live wagering areas, big screens, and serious pageantry.
The evolving Infield experience (21+) featuring music, food, and party-centric vibes. Preakness Stakes – Preakness Official
Pro tips
Buy tickets and lodging early; demand spikes.
Baltimore’s neighborhoods (Hampden, Fells Point, Federal Hill) are perfect for pre/post-race dining.
Artscape (Baltimore): The Nation’s Largest Free Outdoor Arts Festival
What it is: Artscape is Baltimore’s sprawling citywide celebration of visual art, design, performance, music, and food, now re-imagined as a downtown anchor event. The lineup changes yearly, but the spirit stays the same: free expression at scale, neighborhood engagement, and a showcase for regional and national creatives. Visit Baltimore+1
Why it’s epic
It’s free—and huge—making it one of the best family-friendly festivals in the U.S.
Curated installations, interactive exhibits, and vendor markets with local makers.
A perfect window into Baltimore’s creative identity.
Signature experiences
Main-stage music paired with pop-up performances.
Experimental light or public-art activations that transform city blocks.
Pro tips
Use public transit or rideshare; parking fills quickly during peak hours.
Prioritize hydration and shade—summer dates can be warm.
Maryland Film Festival (Baltimore): Indie Cinema, City Soul
What it is: An internationally respected curator of independent film, the Maryland Film Festival (MdFF) brings premieres, filmmaker Q&As, immersive screenings, and tech-forward storytelling to Baltimore’s historic SNF Parkway Theatre each year. It’s a cinephile’s playground—and a great way to support the city’s creative community. Visit Baltimore+1
Why it’s epic
Intimate access to directors and creatives via talks and panels.
A mix of local, national, and international films, shorts, and special programs.
Screenings in a beautifully restored, cinema-loving venue.
Signature experiences
Opening-night features and community-forward events.
Carefully curated shorts blocks—often the festival’s hidden gems.
Pro tips
Plan a schedule: blocks can sell out, and there’s lots to see in a few days.
Explore Station North arts district before/after showtimes for food and galleries.
U.S. Sailboat Show (Annapolis): The World’s Largest In-Water Sailing Show
What it is: Every fall, Annapolis—America’s sailing capital—hosts the U.S. Sailboat Show, drawing boatbuilders, sailors, and dreamers from around the globe. Visitors step aboard the newest designs, shop gear, and take clinics on every aspect of cruising and racing. (There’s a separate Powerboat Show on adjacent dates.) annapolisboatshows.com+2annapolisboatshows.com+2
Why it’s epic
A bucket-list event for sailors and coastal lifestyle fans.
Hands-on demos, navigation seminars, and trip-planning resources.
Downtown City Dock becomes an international marina—photogenic and electric.
Signature experiences
Touring brand-new sailboats and comparing layouts back-to-back.
Gear shopping—foul-weather jackets, electronics, rigging, and more.
Pro tips
Weekdays are quieter; weekends buzz.
Pair the show with historic Annapolis strolls and waterfront dining.
Maryland Seafood Festival (Annapolis): Old Bay, New Memories
What it is: A decades-long Chesapeake tradition, the Maryland Seafood Festival serves up crab cakes, oysters, chef demos, live music, and family activities—often including the beloved Crab Soup Cook-Off. It’s a salty-air celebration of the Bay’s culinary heritage that supports local nonprofits. Visit Annapolis+1
Why it’s epic
A one-stop shop for Maryland seafood classics and coastal vibes.
All-ages friendly with kids zones and artisan vendors.
A chance to sample regional flavors in one place.
Signature experiences
Crab Soup Cook-Off tasting (go hungry).
Live music, chef demonstrations, and cooking tips to bring home.
Pro tips
Arrive early to beat the lunch rush.
Bring a small cooler tote for packaged goods/souvenirs (respect event rules).
National Hard Crab Derby (Crisfield): The Eastern Shore’s Crown Jewel of Crustaceans
What it is: Each Labor Day weekend, Crisfield—“Crab Capital of the World”—throws a spirited festival full of crab races, picking contests, a parade, fireworks, and live entertainment. The National Hard Crab Derby is equal parts wholesome Americana and Chesapeake pride. derby+1
Why it’s epic
Nowhere else will you see crab racing with this much enthusiasm.
A true small-town festival that draws the whole state (and then some).
Waterfront setting at Somers Cove Marina adds postcard views.
Signature experiences
The Crab Picking Contest—local skills on full display.
Derby parade and fireworks capstone.
Pro tips
Book accommodations early—rooms go fast for the holiday weekend.
Pack sun protection; most activities are outdoors along the water.
OC Air Show (Ocean City): Beach, Boardwalk, and Blue Angels
What it is: Summer sky-drama over the Atlantic. The Ocean City Air Show (part of the Air Dot Show tour) features aerial demonstration teams—often including the U.S. Navy Blue Angels—plus vintage aircraft, parachute teams, and premium beach viewing areas. It’s loud, proud, and utterly exhilarating. delmarvanow.com+1
Why it’s epic
Bucket-list flyovers right above Ocean City’s beach and boardwalk.
Family-friendly spectacle with sand-side viewing.
Pairable with classic shore weekend fun.
Signature experiences
Center-point beach tickets for best sightlines.
The visceral roar of afterburners over the surf.
Pro tips
Ear protection for little ones is smart.
Bring light layers—sea breezes can change quickly.
Maryland Sheep & Wool Festival (West Friendship): From Hoof to Handwoven
What it is: One of the largest sheep and fiber festivals in North America, this two-day celebration at the Howard County Fairgrounds packs in hundreds of vendors, farm shows, working dog demos, fleece sales, and workshops for everyone from knitters to shepherds. sheepandwool.org+1
Why it’s epic
A joyful, hands-on look at the fiber arts ecosystem—from animal care to artisan textiles.
Family-friendly education about agriculture and craft.
A shopper’s paradise for yarn, tools, looms, and handmade goods.
Signature experiences
Sheepdog demonstrations and breed showcases.
Fleece & fiber marketplace (arrive early for best selection).
Pro tips
Cashless or card preference can vary by vendor—check onsite notes and bring a backup payment method.
Expect large crowds—arrive early and map your must-see demos.
Maryland Film, Arts, Food… and Heritage Round-Out Pick: Kunta Kinte Heritage Festival (Annapolis)
What it is: A powerful annual celebration of African and African-American culture honoring the story of Kunta Kinte and the broader diaspora. Hosted in Annapolis, the Kunta Kinte Heritage Festival brings music, dance, storytelling, food, artisans, and educational programming to thousands each fall. Visit Annapolis+2Facebook+2
Why it’s epic
Deep emphasis on heritage, perseverance, and community.
Live performances, kid-friendly programming, and vibrant artisan markets.
An important cultural anchor among Maryland’s fall festivals.
Signature experiences
Main stage performances showcasing Afro-diasporic music and dance.
Cultural education zones and heritage exhibits.
Pro tips
Check the official schedule for performance blocks and vendor maps.
Pair with an Annapolis day trip—harbor strolls, museums, and local restaurants.
BONUS ICON: Why These 10 Make the “Epic” Cut
Maryland hosts dozens of annual events, but these ten share the qualities that make a festival trip-worthy and evergreen:
Signature identity: Each event is uniquely Maryland—rooted in the Bay, in Baltimore’s arts scene, or in the state’s agricultural and maritime heritage.
Longevity & scale: These festivals draw regional or national audiences and have either a long historical footprint or a large modern following.
All-ages options: Most offer family-friendly programming alongside adult-oriented fun.
Seasonal balance: From spring film festivals to summer seaside air shows, fall Renaissance revelry, and holiday-adjacent heritage weekends, you can build a calendar of can’t-miss experiences year-round.
Plan Like a Pro: Logistics, Timing, and Insider Strategies
Build your calendar by season
Spring: Maryland Film Festival; Maryland Sheep & Wool (early May); city festivals begin to bloom. Parkway Theatre+1
Early Summer: OC Air Show; coastal getaways and boat-life in full swing. delmarvanow.com
Late Summer / Early Fall: Maryland Renaissance Festival; Hard Crab Derby; Kunta Kinte Heritage Festival; Artscape’s warm-weather iteration. Visit Baltimore+3Maryland Renaissance Festival+3derby+3
Fall (Harbor Season): U.S. Sailboat Show and the Maryland Seafood Festival are prime Chesapeake experiences. annapolisboatshows.com+1
Ticketing & timing
For high-demand events (Preakness, U.S. Sailboat Show), book tickets and lodging early. Visit Baltimore+1
Free festivals (Artscape) still warrant early arrival for parking and best access. Visit Baltimore
Family-friendly playbook
Noise & crowds: Bring ear protection for air shows and plan quiet breaks for littles. air.show
Shade & hydration: Summer events along the Bay can be hot and humid—pack water bottles and hats.
Strollers & terrain: The Ren Fest uses natural surfaces; consider a rugged stroller or carrier. Maryland Renaissance Festival
Transportation & access
Baltimore festivals (Artscape, MdFF, Preakness-adjacent events) are easiest with rideshare or transit during peak hours. Visit Baltimore+1
Annapolis events draw regional traffic; weekday attendance often means smaller crowds. annapolisboatshows.com
Where to stay (high-level)
Baltimore: Downtown/Inner Harbor for walkability to Artscape spillover and MdFF venues; Hampden or Mount Vernon for a boutique vibe. Visit Baltimore
Annapolis: Historic district for walk-to-dock convenience during boat shows and seafood festivities. annapolisboatshows.com
Ocean City: Boardwalk hotels for front-row OC Air Show viewing; consider minimum-night policies during event weekends. air.show
Sample 3-Day “Festival Hop” Itineraries
A. Bay-Lover’s Weekend (Annapolis + Shore)
Day 1 (Fri): Arrive in Annapolis; sunset stroll and dinner near City Dock.
Day 2 (Sat): U.S. Sailboat Show (or Powerboat Show on corresponding dates); afternoon museum or harbor cruise; evening seafood feast. annapolisboatshows.com
Day 3 (Sun): Maryland Seafood Festival tasting sessions; head home with Old Bay on your heart. Visit Annapolis
B. Culture & Cinema (Baltimore)
Day 1: Artscape installations and concerts; late-night dessert in Mount Vernon. Visit Baltimore
Day 2: Maryland Film Festival screenings at SNF Parkway; Q&A with filmmakers. Parkway Theatre
Day 3: Brunch, light sightseeing around the harbor, then head out.
C. Salt-Air Spectacle (Ocean City)
Day 1: Boardwalk rides and beach time.
Day 2: OC Air Show center-point viewing; beach picnic between flight blocks. delmarvanow.com
Day 3: Easy morning swim; drive back via scenic byways.
Frequently Asked Questions (First-Timers’ Edition)
Are these festivals running this year?
Yes—this list focuses on currently operating events with recently published dates or confirmations. Always verify specific dates and ticket policies as calendars shift year to year. delmarvanow.com+7Maryland Renaissance Festival+7Visit Baltimore+7
Which festivals are best for families?
Artscape, Maryland Seafood Festival, Maryland Sheep & Wool, Kunta Kinte Heritage Festival, and Renaissance Festival offer abundant kid-friendly programming. Maryland Renaissance Festival+4Visit Baltimore+4Visit Annapolis+4
What about budget options?
Free or low-cost highlights include Artscape (free), public portions of Kunta Kinte, and parade/fireworks elements at the Hard Crab Derby (some activities may have fees). Visit Baltimore+2Arts Council of Anne Arundel County+2
Do I need to reserve hotel rooms months ahead?
For Preakness, Annapolis boat shows, and peak Ocean City events—yes. Book early for best rates and locations. Visit Baltimore+2annapolisboatshows.com+2
The Top 10, At a Glance
Maryland Renaissance Festival (Crownsville) — Storybook revelry, jousts, artisan markets. Maryland Renaissance Festival
Preakness Stakes Week & Infield Experiences (Baltimore) — Sport, style, and star-powered concerts. Visit Baltimore
Artscape (Baltimore) — The nation’s largest free outdoor arts festival. Visit Baltimore
Maryland Film Festival (Baltimore) — Premier indie cinema and filmmaker Q&As. Parkway Theatre
U.S. Sailboat Show (Annapolis) — The world’s largest in-water sailing show. annapolisboatshows.com
Maryland Seafood Festival (Annapolis) — Crab soup, chef demos, coastal vibes. Visit Annapolis
National Hard Crab Derby (Crisfield) — Crab races, parade, fireworks, and Shore pride. derby
OC Air Show (Ocean City) — Jets over the beach; the Blue Angels frequently headline. delmarvanow.com
Maryland Sheep & Wool Festival (West Friendship) — Farm-to-fiber celebration and marketplace. sheepandwool.org
Kunta Kinte Heritage Festival (Annapolis) — Powerful celebration of African and African-American culture. Visit Annapolis
Conclusion: Make Maryland Your Festival Tradition
If you’re crafting a Maryland bucket list, these ten annual events are your blueprint. They showcase everything the state does best: seafaring heritage, artistic innovation, agricultural pride, cinematic storytelling, world-class sport, and community-first culture. From merrymaking in Revel Grove to savoring crab soup by the Bay, from an air show over the Atlantic to art that takes over city streets, Maryland’s festivals are the kind you don’t just attend—you remember.