Schooner Woodwind Sailing Cruises
For a classic, family-owned sailing experience, choose the Woodwind and Woodwind II. These two beautiful 74-foot schooners are available for 2-hour Public Sailing Cruises, Private Cruises, Schooner Races, Boat & Breakfast Runs, Student Groups, Wine, Beer & Food Events, and for Multi-Day Cruises. Help raise the sails if you wish or simply relax and enjoy a memorable breakfast as it sails past the Naval Academy and cruises into the Chesapeake Bay.
Woodwind and Woodwind II participate in match races every Wednesday night when there is an Annapolis Yacht Club Race. Passengers, otherwise known as guest crew, may participate this is Americas Cup-style racing. Every October, Woodwind races down the Chesapeake Bay to Portsmouth, Virginia with a guest crew for a 130-mile sail, taking as little as 12 hours or as much as 40 hours to complete.
80 Compromise Street, Annapolis, MD 21401, Phone: 410-263-7837
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Road Trip: Great Falls Maryland
The Maryland side of Great Falls is such a great place to explore with kids. The weather this week looks to be less humid and will make for great hiking weather before summer really sets in. The Maryland side of Great Falls offers Mule Drawn Canal Boat Rides and a boardwalk over the falls. If your kids are a little more adventurous hike part or all of the Billygoat Trail for views of the falls and river below. Lots of rock scrambling is required on the Billygoat Trail so proper footware is a must!
Have a great week and leave us your ideas for the best summer activities for kids in Annapolis and well add them to our list. If you are looking for more fun with the kids in Annapolis read our posts What to do with Kids in Annapolis or 50 Things to Do in Annapolis.
Annapolis Canoe & Kayak
Looking for other ways to get out on the water thats a bit more adventurous? Annapolis Canoe & Kayak offers canoe, SUP, and kayak rentals for your whole family.
With over 200 options to choose from, your sure to find something that fits your familys needs. They also provide lessons if you need help teaching your children how to use the gear properly.
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William Paca House & Garden
Built in the 1760s by William Paca, this Georgian manor house is recognized today as one of the finest 18th century homes in the country. In 1901, the property was converted into a hotel, and became Annapoliss finest hotel for decades. Historic Annapolis and the State of Maryland bought the site in 1965 and over the next two decades preserved and restored it to reflect its original 18th century appearance.
Guided tours show off its period furnishings and artwork, and the house is available for hosting special occasions. Using historic scholarship, the 2 acre colonial William Paca Garden has been restored to its former glory. Visitors can enjoy its parterres and terraced gardens, including the Kitchen Garden which provides fresh fruits and vegetables. William Paca was not only a signatory of the Declaration of Independence, but also served as the State of Marylands third Governor. In 1971 this location was recognized as a National Historic Landmark.
186 Prince George Street, Annapolis, MD 21401, Phone: 410-990-4543
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Kunta Kinte/alex Haley Memorial Muse See In Annapolis With Kids

I confess I didnt know the story of this memorial but it is an important one and a great conversation starter for kids when you visit Annapolis. It is located just in front of Rise Up Coffee and at the beginning of the City Dock. Kunta Kinte is a character in the book and miniseries Roots by Alex Haley. He is based on one of his real life ancestors who was enslaved in the Gambia and brought to Maryland around 1767. This memorial is the only memorial in the US that is dedicated to a specific name and place of arrival or an African who was enslaved. Read more on the City of Annapolis website here.
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Visit The Us Naval Academy
Take the kids for a tour of the U.S. Naval Academy, one of the Annapolis greatest sources of pride, and discover what life as a midshipman is really like. If the kids are too young for a guided tour, wander around the campus on your own. During the school year, dont miss the Noon Formation on weekdays when midshipmen form in front of the student dormitory and march into lunch together. Its a ritual not unlike the Changing of the Guard at Buckingham Palace kids will love. Tip: dont forget to bring your passportyoull need a piece of ID to get in.
Find The Best Things To Do With Kids In Annapolis Maryland:
Summer is fast approaching and it is time to plan family adventures with the kids. Find out the best things to do with kids in Annapolis here! Pirate Adventures on the Chesapeake is open for the season in Annapolis, Maryland and is a great way to get the kids out on the water. Annapolis, Maryland is a great family day trip from the Baltimore and Washington DC areas and offers lots of fun places for kids. Start your day with a Pirate Adventure and then spend the day in Annapolis with your family! We have included our Top Ten fun spots to eat and play with the family in the Annapolis area:
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Helen Avalynne Tawes Garden
Tucked among several government office buildings, including the Department of Natural Resources, this garden is named for Mrs. J. Millard Tawes, former first lady of Maryland, from 1959-1967. This 5 acre stretch of greenery is perfect for strolling and discovery, or for relaxing and contemplating.
The garden is situated near the Western Maryland forest, an Eastern Shore peninsula, a stream and several ponds, raised planters and cultivated plantings. Guided tours are free, with a reservation, and the park is open daily, from dawn to dusk. The cafeteria and gift shops are also open daily.
580 Taylor Avenue, Annapolis, MD 21401, Phone: 410-260-8189
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Fort Edward National Historic Site
If you want to get a look at an important part of history, you should make a brief stop at the oldest military blockhouse in North America.
Built by Charles Lawrence in the 18th century, Fort Edward was vital for the English. They used it to guard the road to Halifax. The site was later used as a prison during the Expulsion of the Acadians.
There are also few restaurants in the area if you get hungry, or you can enjoy a picnic nearby.
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Ice Cream In Down Town Annapolis
After all of these fun adventures, your kids are sure to be a bit hungry, so why not treat them to some icecream?
From The Red Bean to Annapolis Icecream Company,Kilwins, and Storm Bros. IcecreamFactory, you and your kids will be sure to find your favorite flavor or several all within walking distance of each other in Downtown Annapolis!
All of these great shops offer unique mixins and flavors and dairy-free alternatives. Try them all, and taste test as you sit along Ego Alley and watch the boats and yachts come in.
Ballocity Indoor Playground At The Annapolis Recreation Center
Often overlooked, Ballocity is a brand new indoor playground at the Roger Pip Moyer Community Recreation Center located on Hilltop Ave. If you are looking for what to with kids in Annapolis on a rainy day Ballocity is a great option. Ballocity is an attraction that features multi-level platforms, interactive blasters, cannons and buckets that propel, throw, and dump thousands of foam balls. If you are looking for more indoor fun for kids on a rainy day find our suggestions at 15 Places for Free Indoor Fun in Maryland and DC.
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The Maryland State House
For those history lovers, the is a must-visit! As the oldest state capitol building that is still in use today, the Maryland State House has been the location of many historical events.
As the Nations Capitol at the end of the American Revolution, the Treaty of Paris was ratified at the Maryland State House in 1784. Also, The Maryland State House was the location that George Washington resigned from Commander-in-Chief of the Continental Army. His resignation allowed him to return to Mount Vernon for a few years of quiet before becoming the first president of the United States of America.
Visit The Historic London Town And Gardens

Take a short drive from the city and make your way to the Historic London Town and Gardens where the original settlement was established during the 17th century. It soon became a significant trade junction, and a few centuries later, it developed into an area that rivaled Annapolis both in size and importance. Visit the town and see it depicted as it once was during its heyday. Youll see costumed interpreters and many interesting buildings, which are either in its original state or had gone through some reconstruction. You can enjoy listening to an overview of the history of the area at the visitors area or on the ground with a guide.
Visit the town and see it depicted as it once was during its heyday. Photo courtesy of Find Your Chesapeake.
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Have Breakfast At Chick And Ruths Delly
There is more than one reason why Chick and Ruths Delly is the place to be for breakfast. First is the amazing food, including our favorite world famous seasoned crab and cheese omelet. Second is the morning ritual.
Every weekday at 8:30am and weekend at 9:30am, the staff of Chick and Ruths assembles for the daily Pledge of Allegiance. Everything and everyone stops for a few brief seconds to salute the flag. Its so unusual, you almost have to see it to believe it. And, depending on the time of year, you may just find yourself standing next to a state legislator or the governor himself. He has his own booth, after all.
Thomas Point Shoal Lighthouse
Built in 1875, the Thomas Point Shoal Lighthouse is the last of its kind, and is one of the most photographed lighthouses in the United States. Tours depart from Annapolis, at waters edge, behind the Annapolis Maritime Museum and all donations go to the upkeep of the lighthouse. The tour of the Lighthouse involves some physical exertion, and a 30-minute boat ride to and from.
You may have a guided tour of the interior of the lighthouse and tours are limited to 18 people per boat. Reservations are required, as is a safety video. Guests are advised to plan ahead as there are no toilet facilities anywhere. Since major exterior preservation work has been done, the focus now turns to finishing the interior of the lighthouse. It has been designated a National Historic Landmark, one of only nine lighthouses in the nation to be given that designation.
723 2nd St, Annapolis, MD 21403, Phone: 415-362-7255
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Quiet Waters Park Best Park In Annapolis With Kids
Quiet Waters Park is just a 10 minute drive from historic Annapolis. It is a really pretty county park right on the water on 340 acres. Since its so big and we only had an hour, we drove all the way down to the water and took the South River Overlook path to the water which was so lovely! It is $6 per vehicle fee and there is lots to explore! From their website: Quiet Waters Park is situated between the South River and Harness Creek. Visitors can enjoy trails winding through forests and past grassy fields, childrens playground, or picnic among 340 acres of beautiful park land.
Tour The Maryland State House
In the heart of Annapolis is the oldest state house in the country thats still in legislative use. It is historic not only because it was Americas capital for nearly a year in 1783-1784 but because several nationally important events happened there.
The is the place where George Washington resigned as commander in chief of the Continental Army and where the Treaty of Paris was ratified. Today, you can visit the Old Senate Chamber and see old George dressed in his finest and letting his intentions be known. Washingtons original address is also on display. A stop at the State House is a quick visit and a must for anyone interested in history.
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Harriet Irving Botanical Gardens
Spend a day with the family at the Harriet Irving Botanical Gardens at Acadia University. The entrance to the Gardens is located off University Avenue, look for the cast iron archway that features the name of the Gardens. Take a stroll along the pathways, admire the wildflowers, relax on the benches, play and cartwheel on the lawns, and have a picnic but remember that there are no litter bins, so pack out what you pack in. Harriet Irving Botanical Gardens
Holiday Extras In Maryland
One of the best parts of winter are the holidays, and there are plenty of extra special events to chase away the chill. Enjoy magical lights at Lights on the Bay, or the Eastport Lights Parade. Cut your own Christmas tree at a local tree farm. Stock up on stocking stuffers at the Anne Arundel Farmers Market Holiday Festival, or explore the Homestead Gardens Christmas shop in Davidsonville. On New Years Eve, watch fireworks from the City Dock. Visit Illuminated London Town for a colonial holiday experience.
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Annapolis With Kids 16 Things To Do In Annapolis For Kids
Annapolis with kids is a wonderful city to explore! It is just a 1 hour drive away from DC and northern Virginia and we had a blast on our recent visit. I didnt realize how many fun things there is to do in Annapolis with kids until I started writing them all down! Below are 16 spots for your familys next adventure including 3 kid-friendly Annapolis restaurants, and then some great family friendly hotels in Annapolis if you want to stay longer than a day!
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Dills Atlantic Giant Pumpkin Farm

The seeds for the biggest pumpkins in the world originated from Howard Dills farm in Windsor. While the original giant pumpkins were just under 500 lbs, the largest pumpkins now weigh over 1 ton.
The experience youll have at Dills Atlantic Giant Pumpkin Farm is truly one of a kind. You can take a walk around the farm and see pumpkins of every size and shape.
To top it all off, Long Pond, located on Dills Farm, is the site of the first hockey game ever. This gives you a chance to visit the birthplace of Canadas most popular sport.
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Evans Family Farm Market
Visit the Largest Corn Maze in the Valley, which is almost the size of a residential subdivision, at the Evans Family Farm in Wilmot. The maze challenge has visitors trying to collect all 6 stamps hidden in the maze, with successful people getting an apple when they finish the maze. The kids will also enjoy the childrens playground, the Pedal Tractor Track, a Pumpkin Cannon, the Big Dig Sandbox and The Pumpkin Train. Evans Family Farm Market Corn Maze