Annapolis is known for its colonial history and sailing tradition, but it’s also a great place to spend time with the whole family. From tours and theatrical performances to on the water activities and festivals, there’s something in Annapolis for everyone no matter the time of year. 


Winter may not seem like a time to get away to Annapolis, but there are plenty of things going on to keep the whole family entertained. Rated one of the ten the best towns in the U.S for the holidays by Travel + Leisure Magazine, Annapolis offers a slew of holiday and seasonal events throughout the winter. There’s also a handful of theatrical performances to keep the little ones – and their parents – entertained. 

Performance Arts

Annapolis is quickly becoming known for its thriving arts and culture scene. From live music to art festivals, it’s the perfect spot to enjoy the work of the area’s talented performers and artists. So, what better way to get into the winter spirit than catching a theatrical performance with the family? Whether it’s watching the Nutcracker put on by the Ballet Theatre of Maryland, It’s a Wonderful Life by the Annapolis Shakespeare Company, or Sleeping Beauty by the Maryland Hall for the Creative Arts, you, and the kids, won’t be disappointed. 

There are also dozens of different classes offered at the Maryland Hall for the Creative Arts, ranging from dance and glass fusing to painting and woodturning. You can find a full list of their classes here


Holiday Events

Consistently ranked one of the best cities in America during the holidays, Annapolis is a great place to spend the weekend enjoying time with family and soaking in the holiday spirit. Here's a list of holiday events to help plan you a holiday excursion in Annapolis. 

  • Midnight Madness – For three Thursday nights in December, stores in downtown Annapolis remain open until 12pm for Midnight Madness, offering shoppers the chance to take care of last minute holiday shopping. You’ll also find live music, activities for the kids, and, of course, Santa. 
  • Lights on the Bay – Held each year at Sandy Point State Park, Lights on the Bay is a drive-thru light show set against the Chesapeake Bay each November through January 1st. Get the whole gang in the car and take a trip through this illuminated winter wonderland.
  • Chocolate Binge Festival – It’s a day full of chocolate, music, and activities. Held on West Street in December, The Chocolate Binge Festival celebrates everything chocolate, and is a great way for anyone with a sweet tooth to spend a day. 
  • Eastport Yacht Club Lights Parade – An Annapolis tradition, the Lights Parade celebrates the sailing culture of the town with a holiday flair. Dozens of boats dazzle onlookers with intricate light displays in the Annapolis Harbor – the perfect way for the whole family to get into the holiday spirit.
  • New Year’s Eve Fireworks – Head down to City Dock on December 31st for a fireworks show in the Annapolis Harbor. There are even cruises you can join to get even closer to all the action. 
  • Maryland Day – In a celebration of Maryland’s birthday, this three-day event offers the kids plenty of events and activities while learning about Maryland’s history.


The arrival of spring means on the water activities like sailing cruises and paddleboarding, historic walking tours to some of the city’s oldest landmarks, and a celebration for graduating United States Naval Academy Midshipmen. 

On the Water Activities

Whether it’s fishing, sailing, cruising, or paddling, Annapolis has a little something for every taste. Rent a paddleboard or kayak and spend an afternoon floating in the Annapolis Harbor or Spa Creek. Climb aboard a fishing charter for a day spent out on the Bay reeling in Rockfish. Or, hop on a schooner and join a sunset sailing cruise to end a perfect day in Annapolis. Looking for a little adventure? Pirate Adventures on the Chesapeake offers short tours of the Harbor where kids dress like pirates in search of treasure. The tours not only allow for a little fun, but include educational lessons regarding the health and wellbeing of the Chesapeake.  

Commissioning Week

Held as one of the most anticipated events of the year in Annapolis, Commissioning Week never disappoints. Even if you don’t know anyone graduating from the Naval Academy, the week-long celebration offers the public a number of chances to witness the aerial acrobatics of the famed Blue Angels. Twice during the week, the Blue Angels fly over the Severn River and the city performing aerial demonstrations for about an hour and a half. Whether you join a sailing cruise to catch the action, or head to the Naval Academy and watch from the banks of the Severn, it’s a can’t-miss event each year. 

Historic Tours

You’ve come to the right town if you’re looking for a little history lesson. With more original 18th-century buildings than any other U.S. city, there’s more than enough to learn in Annapolis. Spend a day touring the Naval Academy, visiting sites like the world-class USNA Museum, the John Paul Jones Crypt, and the USNA Chapel. Or, join a walking tour around the city, stopping in at historic landmarks along the way like the William Paca House (signer of the Declaration of Independence), the Hammond-Harwood House, and the Maryland State House.


Annapolis is on full display in all its glory during the summer. Get on the water. Grab a bite to eat on a rooftop or right on the street. Join a tour or head to one of the many festivals. There’s no shortage of things to do with the family. Here are just a couple of must-dos when taking the family to Annapolis during the summer. 

Fourth of July Parade/Fireworks

Come celebrate America’s birthday in downtown Annapolis. Beginning with a parade, the day-long party offers plenty of activities to do with the whole family before finishing with an impressive fireworks display in the Annapolis Harbor. One of the most-attended events of the year, Fourth of July in Annapolis is sure to keep everyone in the family smiling. There’s even an Independence Day Fireworks Cruise to join, brining you as close as possible to the fireworks above. 

Annapolis Art Week

As the city’s latest event, the Annapolis Art Week has bundled three great art events into one, art-packed week. The week begins with the start of the First Sunday Arts Festival on West Street – an event packed with local artists, food, and music that happens each first Sunday of the month from June through December. Paint Annapolis – one of the city’s favorite art events – takes place throughout the whole week. Painters from all over the region come to Annapolis to paint its scenery., and architecture You’ll see dozens of artists lining the streets in preparation for a juried competition and auction of the artwork at the end of the week.

Last but not least is the Arts & Wine Festival. New to the festival this year is a spotlight of local artists. Aside from all the great Maryland wines on site for tasting, artists from around the area will be in attendance doing live demonstrations. They're also setting up a mural wall that children can help paint through the weekend. There will also be live music and ten different food trucks at the weekend-long event, making for a perfect end to a summer week packed with art.  

Maryland Renaissance Festival

The Maryland Renaissance Festival welcomes visitors to immerse themselves in a recreated 16th century English village. Located at 1821 Crownsville Road in Annapolis, the festival and its village are situated on twenty-five acres of woodland with 85 additional aces set aside for free parking. Take a day to wander through 16th century England while experiencing jesters, jousters, knights, live music, and activities. Hailed as the region's premier outdoor event and the second largest Renaissance Festival in the country with over 280,000 visitors a season, you'll discover a new world full of family-fun, entertainment, food, and more at the Maryland Renaissance Festival.

If you’re looking for more things to do with the kids during the summer, or maybe if you’d like a day to yourself, there are a handful of day camp options in town like sailing camps, programs at Maryland Hall for the Creative Arts, and programs at the United States Naval Academy. 


With the leaves changing colors and a crisp breeze blowing through Annapolis, it’s clear fall has arrived. Though we’re all upset summer has ended, the coming of fall doesn’t mean that things slow down here in Annapolis. From fall festivals and two of the world’s largest in-water boat shows to haunted tours of the city, there are still plenty of ways to enjoy Annapolis with the whole family.

Fall Festivals

The Greenstreet Gardens Fall Festival (391 West Bay Front Road, Lothian, MD 20711) and Homestead Gardens’ Annual Fall Festival (743 West Central Avenue, Davidsonville, MD 21035) are in full swing each weekend throughout the month of October, offering families everything from fun activities like corn mazes and hayrides to pumpkin carving/painting and fresh, seasonal vegetables. Rotating events keep things interesting each weekend, so there’s all the reason in the world to visit more than once.

Historic Ghost Tours

With such a deep-rooted history here in Annapolis, there’s no surprise that ghost tales permeate the town. If you’re looking to get into the spirit of Halloween, there’s no better way than to join a ghost tour. Led by a knowledgeable guide dressed in 18th-century attire, these tours meander through the tight streets of historic downtown Annapolis, stopping at some of the oldest homes and buildings for a quick ghost story. Aside from the scare, the tour gives great insight to the history, tradition, and past lives of Annapolis. 

U.S. Sail/Power Boat Shows

Annapolis is known as the Sailing Capital of the U.S., so it’s no surprise that it’s also home to the world's largest in-water boat shows. During October, two shows come to town: The U.S. Sail Boat Show, and the U.S. Power Boat Show. Vendors line City Dock and Ego Alley, offering everything imaginable to sailors and power boaters from navigational equipment to clothing. There are also hundreds of boats floating in the Annapolis Harbor where attendees can climb aboard and check out the vessels.