By Adam Chubbuck
I have lived and worked in this county long enough to know it by its calendar. Not by the months on a wall, but by the traffic on Generals Highway in October, the masts stacked up at City Dock, the smell of steamed crabs coming off a stadium parking lot in August, and the line of taillights crawling into Sandy Point in December.
I am Adam Chubbuck, Team Leader of Team Alpha Charlie of Douglas Realty. I am a retired Navy Chief, a Tom Ferry business coach, and a full-time Realtor who has closed more than 350 homes over the last five years across the Baltimore to Annapolis corridor. That work has taken me into just about every neighborhood in this county, from Glen Burnie to Edgewater, from Crofton to Cape St. Claire.
Here is what I have learned. People do not buy a house. They buy a life, and the events on this list are a big part of what that life looks like here. Knowing your community makes you a better neighbor first and a better Realtor second. So here are 21 annual Anne Arundel County traditions worth putting on your calendar.
1. Maryland Renaissance Festival
The Maryland Renaissance Festival is the largest annual event in the county by attendance, and it runs on weekends from late August through late October in Crownsville. The festival grounds are a permanent village built into the woods off Crownsville Road, with stages, shops, jousting arenas, and food stalls that only wake up for those nine or ten weekends a year.
Why locals love it
It is a rite of passage. Kids in Severna Park and Millersville grow up going, then come back as teenagers with friends, then bring their own children. Season passes are common in this county for a reason.
Insider tip from Adam
Go on an October Sunday rather than a September Saturday. The weather has broken, the crowds are lighter, and the drive in on Route 178 moves. Get there when the gates open and park in the near lots before the lines back up onto General’s Highway. Buyers looking in Crownsville, Millersville, and Arnold should know that festival weekends change the traffic pattern in that corridor. When I show homes out there in the fall, I plan the route around it.
2. Annapolis Boat Shows
The Annapolis Boat Shows are the reason people around the world know this town. The shows take over City Dock and the surrounding harbor with floating docks, tents, and hundreds of boats you can actually walk aboard.
The spring sailboat show
Every April, the spring sailboat show opens the season with new and brokerage sailboats, catamarans, gear vendors, and a tasting tent. It is smaller and easier to navigate than the fall shows, which is exactly why locals like it.
The fall shows
In October, the powerboat show and the sailboat show run on back to back weekends at City Dock. These are among the largest in-water boat shows in the country, and they have been running for more than fifty years. Downtown fills up, the restaurants run wait lists, and the whole city smells like diesel and crab dip. Across the Bay Bridge in Stevensville, the same organization runs a spring show at Bay Bridge Marina if you want another look at the water.
Insider tip from Adam
Buy a weekday ticket if you can take the time off. Thursday and Friday are for people who are actually shopping for a boat. Saturday is for the crowd. Park at Navy-Marine Corps Memorial Stadium and take the shuttle. Do not try to find a spot downtown. If you are thinking about a waterfront or water-privileged property, boat show week is the best week of the year to walk the docks and figure out what size slip you actually need. That conversation shapes the search, and it is one I have with clients every fall. You can search Anne Arundel County homes with water access when you are ready.
3. Maryland Seafood Festival
The Maryland Seafood Festival is held every September at Sandy Point State Park, on the beach with the Bay Bridge in view. It dates back to the 1960s and it is the closest thing this county has to an official celebration of what we eat.
The crab soup cook-off is the centerpiece. Local restaurants bring their best Maryland crab soup and cream of crab, you get a spoon and a ballot, and you work your way down the line. Beyond the soup there are seafood vendors, a beer and oyster tent, live music on the sand, and artisan booths.
Insider tip from Adam
Get there early on Saturday and go straight to the soup tent. It runs until the soup is gone, not until the clock says stop. Parking at the park fills fast, so use the shuttle from Anne Arundel Community College in Arnold when it is offered. Bring cash, bring a chair, and wear shoes you do not mind getting sandy.
4. Lights on the Bay
Lights on the Bay is the holiday light show at Sandy Point State Park, running nightly from late November through New Year’s Day. It is a roughly two mile drive through the park with around 70 animated and stationary displays, and proceeds support the SPCA of Anne Arundel County. It has been going for more than three decades.
Why locals love it
You stay in your car. That matters when it is 34 degrees and you have a toddler in a car seat. Families make a night of it with hot chocolate and a Christmas playlist, and the displays include Annapolis and Chesapeake themes you will not find at a generic light show.
Insider tip from Adam
Go on a weeknight in early December. Weekend nights close to Christmas can back the line up out to College Parkway. Buy tickets online ahead of time to move faster at the gate. If you have a dog, watch for the special walk-through nights they hold each season.
5. Fourth of July in Annapolis
The City of Annapolis celebrates Independence Day with a parade and a fireworks display over the harbor. The parade runs along West Street, around Church Circle, and down Main Street toward the water. In the evening, the fireworks go off over Spa Creek and the harbor, and the whole waterfront turns out for it.
Where to watch
The seawall at City Dock is the postcard view and the most crowded. Locals spread out to the Eastport side, to Truxtun Park, to the Naval Academy Bridge, and onto boats anchored off the harbor. If you know somebody with a boat in Eastport or Bay Ridge, that is the ticket.
Insider tip from Adam
Park once and walk. Downtown streets close, and the garages empty slowly after the show. My honest recommendation is to skip the drive entirely, park in Parole or near West Street early in the day, and make a full day of it. As a Navy retiree, I will also say this. Watching fireworks go up over the Naval Academy with a crowd of veterans, midshipmen, and families around you is worth the parking headache.
6. Anne Arundel County Fair
The Anne Arundel County Fair has been running since 1952 and takes place every September at the fairgrounds in Crownsville. Livestock shows, 4-H exhibits, home arts and baking competitions, tractor pulls, a rodeo, carnival rides, and a midway full of fair food.
Why locals love it
This is the part of the county people forget exists. Anne Arundel still has working farms in the south county and out toward Davidsonville and Lothian, and the fair is where those families show what they have raised and grown all year. Kids from Crofton and Odenton who have never touched a goat get to touch a goat.
Insider tip from Adam
Go on a weekday evening. Admission lines are short, the animal barns are calm, and you can actually talk to the 4-H kids about what they brought. Bring cash for the food booths run by local churches and fire companies. That money stays here.
7. Commissioning Week at the Naval Academy
Commissioning Week takes place in late May at the United States Naval Academy and marks the graduation of the firstie class. The week includes parades, the Herndon Monument climb by the plebe class, concerts, and the graduation ceremony itself at Navy-Marine Corps Memorial Stadium.
Insider tip from Adam
Downtown Annapolis is at capacity that week. Hotels are booked, restaurants need reservations, and traffic on Rowe Boulevard and King George Street backs up. If you have a settlement or a showing scheduled in the historic district during Commissioning Week, build in an extra half hour. As a retired Chief, I will tell you the Herndon climb is worth seeing once in your life. It is a couple thousand young people solving one problem together in the mud.
8. Blue Angels Week
The Blue Angels perform over the Severn River during Commissioning Week each May. The jets come in low over the river with the Academy, the Naval Academy Bridge, and the Annapolis skyline underneath them, and the whole city stops to look up.
Insider tip from Adam
There is typically a practice day before the main performance, and the practice is often the better experience. Smaller crowds, same jets. Popular viewing spots include Jonas Green Park, the Naval Academy Bridge sidewalk, and boats anchored in the Severn. If you live in Arnold, Cape St. Claire, or on the water in Eastport, you have a front porch seat. I have had buyers put an offer on a house that week specifically because they walked outside and saw that.
9. Annapolis Cup Croquet Match
Every April, St. John’s College and the United States Naval Academy meet on the front lawn of St. John’s for a croquet match that has been running for more than four decades. Midshipmen in dress whites, St. John’s students in seersucker and boater hats, picnic blankets, brass bands, and thousands of spectators.
Insider tip from Adam
Arrive early with a blanket and stake out lawn space near the ropes. It is free to attend and it is one of the more genuinely charming afternoons on the Annapolis calendar. Dress the part. People take the outfits seriously, and half the fun is watching them do it.
10. Kunta Kinte Heritage Festival
The Kunta Kinte Heritage Festival began in Annapolis in 1987 and is held in early fall. It celebrates the heritage, perseverance, and cultural contributions of Africans, African Americans, and people of African descent from the Caribbean, anchored to the history of the Annapolis waterfront where Kunta Kinte arrived in 1767.
Expect live music, dance, storytelling, artisan vendors, and food. It is volunteer run and community built, and that shows in the feel of it.
Insider tip from Adam
Pair the festival with a walk to the Kunta Kinte and Alex Haley Memorial at City Dock. If you are new to Annapolis, that memorial and the story behind it will tell you more about this town in fifteen minutes than any guidebook.
11. Annapolis Irish Festival
The Annapolis Irish Festival is a summer tradition at the Anne Arundel County Fairgrounds in Crownsville. Multiple stages of Celtic and Irish rock music, pipe bands, Irish dance, vendors, food, and a well-attended beer tent under the trees.
Insider tip from Adam
The fairgrounds are grass and gravel, so wear real shoes. Bring lawn chairs, because seating is what you carry in. It is an easy drive from Crofton, Odenton, and Severna Park, and it is one of the few large festivals in this county where the parking is not a fight.
12. First Sunday Arts Festival
From May through November, inner West Street in Annapolis closes to traffic on the first Sunday of each month for the First Sunday Arts Festival. More than a hundred vendors set up with art, crafts, jewelry, and food, with live music and cafe style dining down the middle of the street.
Insider tip from Adam
This is the best low-commitment way to get to know the Annapolis Arts District. It is free, it is walkable, and it repeats every month for seven months, so there is no pressure to make any single one. I send new-to-the-area clients here constantly. Walk West Street on a First Sunday and you will understand the neighborhood better than any listing description could explain it. When you are ready to look at what is available nearby, you can start your home search with our team.
13. Eastport Yacht Club Lights Parade
On the second Saturday of December, decorated and illuminated boats parade through Annapolis Harbor and Spa Creek from about 6 p.m. to 8 p.m. Crews spend weeks wiring their boats, and the results range from tasteful to gloriously ridiculous.
Where to watch
Spectators line City Dock, the Eastport side of Spa Creek, Annapolis Maritime Museum, and the Spa Creek Bridge. Waterfront restaurants and homes along the creek fill up with parties.
Insider tip from Adam
Dress warmer than you think you need to. Wind off the water in December is a different animal. Get in position by 5:30 for a spot with an unobstructed sightline. If you are house hunting in Eastport, this is the night that explains why people pay what they pay to live there.
14. Annapolis Film Festival
The Annapolis Film Festival runs in the spring and screens more than 70 films over four days at venues around the city, including Maryland Hall. It is built around panel discussions, post-screening question and answer sessions with directors, and coffee talks with industry people.
Insider tip from Adam
Buy a pass instead of individual tickets if you plan to see more than three films. Read the schedule ahead of time and pick the shorts blocks, because that is where the surprises are. Venues are spread across town, so leave travel time between screenings.
15. Annapolis Rotary Crab Feast
The Rotary Club of Annapolis holds its crab feast every August at Navy-Marine Corps Memorial Stadium. Steamed crabs, crab soup, barbecue, corn on the cob, and beverages, served under the stands and out on the concourse. Proceeds go to local charities, and the club has awarded well over a million dollars in community grants through the program.
Why locals love it
It is the crab feast every other crab feast in this county is measured against. It is also a genuinely good cause, which is how we do things here. Fire companies, churches, sports boosters, and civic associations across Pasadena, Glen Burnie, and Severna Park run their own crab feasts all summer for the same reason.
Insider tip from Adam
Wear clothes you do not care about and bring your own crab mallet if you have a favorite. Pace yourself early. The line at the crab tables moves in waves, and the people who sprint out of the gate are done by hour two.
16. Grand Illumination and Christmas in Annapolis
The holiday season downtown officially opens with the Grand Illumination and tree lighting near Market House on the Sunday after Thanksgiving. It is free, it is family focused, and it comes with carolers, music, and the arrival of Santa. Through December, Midnight Madness keeps the shops on Main Street, West Street, Maryland Avenue, and State Circle open late on Thursday evenings, with decorations, entertainment, and refreshments the whole way down.
Insider tip from Adam
Do your Christmas shopping on a Midnight Madness Thursday. The stores are open late, the streets are lit, and you are keeping money with local independent businesses instead of a warehouse in another state. Park in a garage and walk. Main Street is a hill, so wear shoes you can handle it in.
17. Severna Park Fourth of July Parade
Severna Park runs a hometown Independence Day parade on the morning of the Fourth. Fire apparatus, scout troops, little league teams, civic associations, veterans groups, classic cars, and candy thrown to kids on the curb.
Why locals love it
This is small town America inside a Baltimore-Annapolis suburb, and it is one of the reasons families keep choosing Severna Park. You see your neighbors, your kid’s teacher, and the guy who fixed your HVAC, all in the same two hours.
Insider tip from Adam
Stake out curb space early with chairs, and bring a bag for the candy. Go to the parade in the morning in Severna Park, then head into Annapolis for fireworks that night. That is the full county Fourth of July, and it is how a lot of families around here do it. I have sold plenty of homes in these neighborhoods, and I can tell you the parade route address premium is real in July. If you want to connect with Team Alpha Charlie, we know these streets block by block.
18. Annapolis St. Patrick’s Day Parade and Weekend
Annapolis celebrates St. Patrick’s Day with a parade and a full weekend of festivities in the historic district. Pipe bands, Irish dance schools, civic and community groups, and a downtown that turns green for a few days.
Insider tip from Adam
The parade is family friendly during the day, and the atmosphere changes after dark. Plan accordingly depending on who you are bringing. Public transportation and rideshare are the smart call. It is March in Maryland, so bring layers and expect anything from 30 degrees to 65.
19. Maryland Day Celebration Weekend
Maryland Day commemorates the founding of the Maryland colony and is celebrated over a weekend in March across Annapolis and southern Anne Arundel County. Dozens of historic sites, museums, and cultural locations open their doors for free or for a nominal admission, usually a dollar.
Why locals love it
You can walk into places you drive past every day and never enter. Historic homes in Annapolis, museums, gardens, and heritage sites down toward Edgewater and South County all participate.
Insider tip from Adam
Pick a geographic cluster rather than trying to hit everything. Do the historic district on foot one day, or take a run down Route 2 through Edgewater and hit the South County sites. This weekend is the single best value on the county calendar for families, and it is a great way for new residents to build a mental map of where they actually live. That local knowledge is exactly what I try to give clients, and you can learn more about our team and how we work.
20. Annapolis Chocolate Binge Festival
Held on the first Sunday of December on inner West Street, the Annapolis Chocolate Binge Festival brings chocolate vendors, family entertainment, holiday shopping, and the West Street holiday light canopy overhead. Truffles, fudge, cookies, cakes, brownies, and a few things you would not think to put chocolate on.
Insider tip from Adam
Take the kids in the early afternoon before the crowd thickens. Bring cash for the vendors and go with a plan, because standing in the middle of West Street trying to decide is how you lose an hour. Combine it with holiday shopping on the same block and you have handled two things at once.
21. Annapolis Songwriters Festival
Each September, the Annapolis Songwriters Festival brings performing songwriters into venues across the city for multi-day rounds of shows. Modeled on the Key West festival of the same style, it puts the writers behind well known songs on small stages in a town built for exactly that.
Insider tip from Adam
The magic is in the smaller rooms, not the headline slots. Look at the venue list, pick two rooms within walking distance of each other, and let the night happen. September in Annapolis is the best month of the year here, and this festival lands right in it.
More County Traditions Worth Knowing
A few more that regularly earn a place on the calendar around here. Anne Arundel County Arts Month each June, with events across the county. Paint Annapolis, the juried plein air painting competition that puts artists on street corners all over the historic district. The Annapolis Juneteenth Parade and Festival downtown in June. Dinner Under the Stars, when the first block of West Street becomes an outdoor dining room on evenings from spring into early fall. The Great Annapolis Pumpkins that show up downtown in October. Small Business Saturday and Annapolis Restaurant Week, both of which are worth timing a trip downtown around. And the New Year’s Eve celebration at City Dock, with an early family fireworks display and a second one at midnight.
Why This List Matters If You Are Buying or Selling Here
Every one of these events happens in somebody’s neighborhood. The Renaissance Festival is somebody’s commute in October. The boat shows are somebody’s parking situation. The Severna Park parade goes down somebody’s street. When I help a family buy a home in Anne Arundel County, I am not just running comparable sales. I am telling them what their October looks like, what their Fourth of July looks like, and what it feels like to live there in December.
That is the difference between a Real Estate agent who sells in a county and one who lives in it. I have been here, I serve clients here, and I have helped hundreds of families land in the neighborhoods that host these traditions.
Ready to Find Your Place in Anne Arundel County
If you are thinking about buying or selling in Annapolis, Severna Park, Pasadena, Arnold, Crofton, Odenton, Glen Burnie, Edgewater, or anywhere else in Anne Arundel County, I would like to help. Whether you are a first time buyer, a military family with orders to Fort Meade or the Naval Academy, or a homeowner deciding what your property is worth in today’s market, the conversation starts the same way. Tell me what you want your life here to look like, and I will tell you where that lives.
Adam Chubbuck, Team Leader, Team Alpha Charlie of Douglas Realty Website: https://TACMD.COM Email: [email protected] Phone: 443-347-6692
Smile more, Adam Chubbuck
Frequently Asked Questions About Anne Arundel County Events
What is the biggest annual event in Anne Arundel County?
The Maryland Renaissance Festival in Crownsville draws the largest attendance of any annual event in Anne Arundel County. It runs weekends from late August through late October. The Annapolis Boat Shows in October are the county’s most internationally known events and fill downtown Annapolis to capacity.
When are the Annapolis Boat Shows?
There is a spring sailboat show at Annapolis City Dock every April, and two fall shows in October, a powerboat show and a sailboat show, held on back to back weekends. All three take place in the water at City Dock in downtown Annapolis. The fall shows have been running for more than fifty years.
What are the best free things to do in Anne Arundel County each year?
The First Sunday Arts Festival on West Street from May through November is free, as is the Grand Illumination tree lighting the Sunday after Thanksgiving. The Annapolis Cup croquet match, the Severna Park Fourth of July Parade, the Annapolis St. Patrick’s Day Parade, and the Blue Angels flyover during Commissioning Week are all free to watch as well.
Where can I watch the Blue Angels in Annapolis?
The Blue Angels perform over the Severn River during Commissioning Week at the Naval Academy in late May. Common public viewing spots include Jonas Green Park, the sidewalk on the Naval Academy Bridge, and the waterfront in Eastport and Arnold. There is typically a practice day before the main performance that draws smaller crowds.
What annual events happen outside of Annapolis in Anne Arundel County?
The Maryland Renaissance Festival, the Anne Arundel County Fair, and the Annapolis Irish Festival all take place in Crownsville. The Severna Park Fourth of July Parade runs through Severna Park. Community crab feasts, church festivals, and fire company carnivals happen throughout the year in Pasadena, Glen Burnie, Odenton, Crofton, and Edgewater.
When is the Maryland Seafood Festival and what happens there?
The Maryland Seafood Festival is held every September at Sandy Point State Park in Annapolis. The crab soup cook-off is the main draw, with local restaurants competing in Maryland crab soup and cream of crab categories. The festival also features seafood vendors, a beer and oyster tent, live music, and artisan booths on the beach.
What is the best time of year to visit Anne Arundel County?
September and October are the strongest months on the local calendar. That window includes the Maryland Seafood Festival, the Anne Arundel County Fair, the Kunta Kinte Heritage Festival, the Annapolis Songwriters Festival, the Maryland Renaissance Festival, and the fall Annapolis Boat Shows. The weather is usually excellent and the Chesapeake Bay is at its best.
How do local events affect home values in Anne Arundel County?
Proximity to events and amenities affects buyer demand in specific neighborhoods, particularly waterfront and water-privileged properties in Eastport, Arnold, Cape St. Claire, and Pasadena, and walkable homes in downtown Annapolis and Severna Park. Event access is one factor among many, alongside schools, commute, condition, and water depth for boat owners. A local agent who knows these neighborhoods can tell you which factors actually move price in a given block.
About Adam Chubbuck
I am Adam Chubbuck, Team Leader of Team Alpha Charlie of Douglas Realty. I am a retired United States Navy Chief and a licensed Real Estate agent in Maryland and Virginia, serving the Baltimore to Annapolis corridor with a focus on Anne Arundel County. Over the last five years I have closed more than 350 homes, and I work with a lot of military, veteran, and Department of Defense families moving to Fort Meade, the Naval Academy, NSA, and the surrounding commands. I am also a Tom Ferry business coach, which means I spend part of my week teaching other agents how to do this work well.
I live here. I raise a family here. I know which streets flood, which schools people fight to get into, which neighborhoods empty out on a Saturday in October because everybody is at the Renaissance Festival. That is the kind of information that does not show up in a listing description, and it is the reason clients call me.
If you are buying, selling, investing, or just trying to figure out what your home is worth right now, reach out. No pressure, no pitch, just a straight answer.
Adam Chubbuck Team Leader, Team Alpha Charlie of Douglas Realty Website: https://TACMD.COM Email: [email protected] Phone: 443-347-6692 Serving Annapolis, Severna Park, Pasadena, Arnold, Millersville, Crofton, Odenton, Glen Burnie, Edgewater, and all of Anne Arundel County
Smile more, Adam Chubbuck
