10 Awesome Annapolis Events You Must Attend in Summer

Sometimes you just have to escape the city heat in Washington, D.C. and head to the Chesapeake Bay. Annapolis events are the best way to eat great food, do a little shopping, see the historic colonial sites of Maryland and enjoy the summer sun on the water in the sailing capital of Maryland.

After all, there is no end to things to do in Annapolis with kids in the summertime.

Annapolis Events- Summer

Don’t know which events to attend? We’ve got a few ideas, including both summer-long and annual events, July 4th entertainment, and hotels to crash in when you just can’t stand the thought of only spending a day in the Maryland state capital.

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Summer Events in Annapolis with Kids

There are loads of annual events in Maryland’s capital city and activities all summer long that you don’t want to miss, including:

  • Annapolis Arts and Wine Festival (June)
  • Annapolis Irish Festival (June)
  • Annapolis Leukemia Cup (June)
  • Bands in the Sand (June)
  • Wednesday Night Sailboat Races (June through August)
  • First Sunday Arts Festival (Firsy Sunday of July, August and September)
  • Rotary Club of Annapolis Crab Feast (August)
  • Kegs and Corks Craft Beer and MD Wine Festival (August)
  • Annapolis Art Walk (August)
  • Maryland Renaissance Festival (August through October)

NOTE: Check website for exact dates and times as they do change from year to year.

While many of these events are kid friendly, you don’t actually have to take the kids with you. Enjoy a cold brew or a glass of wine with your loved one. You deserve a night out on the bay.

Celebrate the Fourth of July in Annapolis

Of course, you can’t celebrate the Fourth of July in the state capital without an all-out extravaganza, which includes fireworks, a United States Naval Academy Band concert, and a 4th of July day parade down West Street.

The streets will be a madhouse, so park your car at your hotel and plan on walking as much as possible to the city’s numerous events in the arts district and near the city dock.

If you have children with you, bring that small, fold-up umbrella stroller for when those little legs get tired.

Fireworks at Home

In the city of Annapolis, you can legally personally use sparklers, fountains, crackle, strobe, wheels, spinners and certain novelty fireworks on the 4th of July.

Please remember that it is illegal to cross state lines and import fireworks for backyard celebrations. Hefty fines will be dealt to anyone caught setting off illegal fireworks. These can include up to $250,000 and 25 years in prison for larger fireworks.

Each Maryland county has its own fireworks laws when it comes to smaller fireworks, so do your research before you use an fireworks at home.

Perfect Annapolis Family Hotels

Annapolis is a great day trip when you are looking for more things to do in D.C., but it can easily be a weekend getaway too. Book a hotel, spend a few days exploring the Chesapeake Bay and dive into what makes this state capital so great. No need to do a crazy amount of research—we already did it for you!

Find your perfect Annapolis Hotel:


Washington, D.C. Travel Resources

Your Washington, D.C. vacation doesn’t have to be stressful. We’ve got the resources you need to plan your trip and make the most out of your time in the city and surrounding area. If this is your first time to the capital region, check out our Washington, D.C. trip planner and itineraries.

For transportation, check out our D.C. driving guide and our guide on how to ride the metro. For those flying in, you’ll want to read our guides to BWI, DCA and IAD airports.

Dive into our things to do in D.C., which is always being updated and evolving to make sure you have the latest and greatest activities to fill your checklist of things to do. Don’t forget about food, the real reason we all travel, right? Our Washington, D.C. restaurant guide will get you started and lead you into neighborhoods full of delicious treats.

For more resources, check out our pages on Baltimore, Frederick,Richmond, Virginia Beach, Williamsburg, Shenandoah National Park and beyond.

Where to Stay in Washington, D.C.

Budget: When it comes to Washington, D.C. budget hotels, prices vary depending on the season. In the middle of October, a four-star hotel could be under $150, while in December it may be over $400. At any given time of year, though, Hotel Hive is a safe bet for value when it comes to resting your head. If you are looking for a hostel, Hi Washington D.C. Downtown is well located for exploring all of the D.C. museums, restaurants and bars at the fraction of the price of a hotel. Check rates and availability here.

Mid-range: Every USA hotel chain can be found in Washington, D.C., but stay at the St. Gregory Hotel when you want a local touch. The modern, light-filled rooms will welcome you to the city, whether you are in a studio or suite with wraparound terrace. The hotel is walking distance to Georgetown, the National Mall and Embassy Row, making it easy to explore without a rental car. Check rates and availability here.

Luxury: You are spoiled for choice when it comes to luxury hotels in Washington, D.C. We love cozying up at the Graham Georgetown, a sweet little boutique hotel in one of the hottest neighborhoods in the city. Check rates and availability here. Major hotel brands like The Fairmont, Mandarin Oriental, Ritz-Carlton, Four Seasons Hotel Washington D.C. and St. Regis Washington D.C. all have outposts here as well. If you want something a bit more historic, we recommend The Jefferson, Washington D.C. Ninety-nine rooms in this luxury boutique hotel bring together an attentive staff, petite spa, and the Michelin-starred Plume restaurant with all of the history you could hope for when you are in the nation’s capital. Check rates and availability here.

Family-friendly: We always gravitate towards the Kimpton hotels whenever we are traveling with kids. Kimpton Hotel Monaco Washington D.C., once the General Post Office building, is located in the Penn Quarter neighborhood just four blocks off the National Mall near the National Gallery of Art. Price point is mid-range, depending on the time of year you visit. Parents will love the nightly wine events and evening nightcap perks as well as complimentary coffee and a tea bar each morning. Kids will love that they can borrow a fish friend for their stay, and that there is always a treat on hand that they can enjoy, and the robes are just their size. Kimpton also has adult and child-size bikes to borrow so you can cruise around town during your stay. Check rates and availability here.

Looking for Washington DC Rentals? Check HERE for the best location, size and rates.

Washington DC Rental Car

If you just flew in , you probably need a rental car. Although you can certainly take the Metro most places, especially if you fly into DCA, you may want a rental car to get out and explore. Find the best priced and availability HERE.

Planning a Trip to Washington, D.C.? Don’t Forget Travel Insurance!

Whether you are traveling domestically or coming from an international destination, travel insurance is a must for anyone coming to Washington, D.C. You will be exploring both inside and outdoors; hiking may even happen if you get adventurous. You could find yourself on a Segway or bike tour. The city is highly populated and accidents and crime do happen. This is not to scare you, but to prepare you for what could occur when you are checking out the free museums, exploring neighborhoods, finding the best food and learning about the local street art. Should something happen, travel insurance has you covered.

We recommend and use Allianz Travel insurance. Our family is covered under a household plan, but their individual plans are just as robust if you are a solo traveler or a couple looking to get away. I’ve been a customer for more than five years and have always been in good hands with the Allianz team.

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