Things to do in Annapolis

The Ultimate Annapolis Summer and Fall Guide

As you begin traveling once again, you may just be realizing that although summer is the typical vacation time, it is not the only time to explore new places. The feel of the season and the activities you may take part in may be different, but when you choose At Home Annapolis for your Maryland journey, the warmth, welcoming, and quiet luxuries found in our properties remains the same! This guide to the beauty of our homes will entice you to stay, and this guide to all the fun you can have in the summer in Annapolis and in the fall will convince you that there is no better vacation than one spent in Maryland under the roofs of any of our At Home Annapolis seasonal sanctuaries!

Step into Comfort

As to be expected, each of our At Home Annapolis vacation escapes are destined to be unique, designed to match the homeowner’s tastes, which gives our guests plenty of options when it comes to picking the vacation home of their dreams! Pick a waterfront property in which you will want to spend as much time outside as in. Lounge in a hammock under a tree, contemplating adventures you will take in that rental boat tied to your private dock, or sit on a deck watching the activity on the water below you. These outdoor activities will enhance the wonders found inside, where the kitchens are the heart of the home, the dining rooms are where many memories will be made, and bedrooms will offer the ultimate in luxuries—a deep sleep that is uninterrupted and peaceful!

Choose a home close to the US Naval Academy, ensuring that all the activities of Commissioning Week are within a short distance, allowing you to nap on soft couches, practice cannonballs in private pools, or gather around a firepit, reminiscing about your graduate’s youth and wondering how time passed by so fast! You can also reserve one of our pet-friendly rentals, offering all the wonderful qualities of our non-pet-friendly ones but with the added benefits of being able to relax, explore, and hang out with ALL the members of your family. Your most loyal of companions can run in fenced-in backyards and nap in front of a merrily crackling fire on a cool autumn day. Reserve a 7 bedroom “estate” and celebrate a holiday with friends, family, and loved ones; prepare feasts in kitchens with large breakfast bars and updated appliances, start a pool championship and wait until the last day to release your inner pool shark, or use a rainy day as an excuse to hang out in theater rooms, watching old movies that never lose their charm!

You could visit Annapolis a hundred times and experience 100 different realities, but all vacations spent with At Home Annapolis are guaranteed to be filled with love, laughter, and comfort. Memories are made in our homes, and the vacation you have here will be the first one you wished would go on forever!

Summer in Annapolis

Summer Living

Every season is the best time to visit Annapolis, but summertime brings along a certain laidback vibe that is relaxing and fun! Commissioning Week has ended, the sailor/students have gone back to their hometowns or on to their first adventure as a commissioned officer, and the longer lines at restaurants die down just a little.

Take the time to visit the homes of former Declaration of Independence signers—there are four in Annapolis out of only 15 left in the entire nation—and walk in the steps of the brave men who lived there. The William Paca House, built in 1763 and located at 186 Prince George Street, is one of our favorite places to visit in the summer in Annapolis. Offering beautiful gardens that come to life during this sultry season, it is easy to spend an entire day just walking and enjoying the outdoors, but now that the house itself has opened again, you must go inside! Daily tours are offered every day of the week on the half hour and they are open from Monday through Saturday from 10 AM until 5 PM, and Sundays from 11 AM until 4 PM. The Banneker-Douglass Museum, located at 84 Franklin Street, is not a home of a former signer, but it does offer an extensive display of African American history that is fascinating and informative!

After all this history, you may feel the need for a treat (we will discuss local restaurants in another paragraph!) and there is no activity more summery than a visit to the Annapolis Ice Cream Company on Main Street! Featuring delicious ice cream cakes if you are celebrating a special birthday during your trip and offering an expansive variety of flavors that change on a daily basis, there is no greater pleasure in Annapolis than enjoying a scoop of Oreo flavored ice cream topping a waffle cone as you sit on a bench at City Dock, watching the parade of boats floating by on the bay. Ego Alley is another place to get a good look at the beautiful vessels that float on the waters in the area, and speaking of boats, if you want to do more than watch the fun, Watermark Tours offers a variety of options for doing so! Continue your explorations of Annapolis on sightseeing cruises that take you on the Harbor, Spa Creek, the Severn River, and Chesapeake Bay! Getting from place to place via speed boat is a fun way to see the city and is an activity you can partake in aboard a water taxi, also offered by Watermark Tours. When you want to do something that will really make the people back home feel jealous, take a weekend to learn to sail at the Annapolis Sailing School. Who knows? Maybe when you return to your own hometown, this new hobby will change the way your weekends look!

Finally, our last adventure of the summer is also on a boat and is one that will make you a hero in your children’s eyes! Pirate Adventures of the Chesapeake docks on 3rd Street and is literally the most fun you can have on the water. Offering pirate costumes and face paint, water cannons with bad guys who tried to come aboard, dancing, singing, pirate language lessons, and a chance to earn some pirate’s treasure, this adventure is truly one your child will never forget, and parents have a great time as well!

Fall in Annapolis

Fall Flings in Annapolis

The end of summer brings us to quite possibly our favorite season of all, and if your life’s journey brings you to our city on the bay in the fall, you will soon see why! The weather changes from sultry to crisp, the smell of fireplaces burning for the first time of the season wafts through the air, and the trees that dot our landscape offer explosions of fiery color as they dress in their fall finest. This is when you will see the locals coming out to play, hiking and exploring the natural landscape of parks such as Quiet Waters, Broad Creek Park, and Poet’s Nature Trail. Football is popular all over the nation at this time, and tailgate parties are held in the parking lot of the Navy-Marine Corps Memorial Stadium during home games.

In 2021, the US Powerboat Show comes to town October 7th-10th. Conveniently for boat lovers, the US Sailboat Show takes place the week after, October 14th through 18th, so if you are in the market for a new power or sailboat or if you just want to take a peek at the pretty vessels and learn how the other half lives, be sure to mark your calendar and plan your escape this fall in Annapolis to encompass both weekends and experience the time of your life!

October is a pretty popular month in Maryland, as we attend boat shows, drink pumpkin spice everything, and prepare for the spookiest holiday of the year! We decorate the restaurants, shops, and bars in shades of orange and black, plan our Halloween costumes, and for those who take the holiday seriously, participate in ghost tours given by Annapolis Ghost Tours & Crawls! The Haunted Pub Crawl of Historic Annapolis is a fantastic way to scare yourself and enjoy a few drinks along the way, and yes, chances are you will find some pumpkin spice beers in at least one of the stops. At the time of this writing, we can not guarantee the construction of any haunted houses, but historically, Leach Woods at 1001 Chesterfield Road has offered up a Halloween festival that includes corn mazes, hay rides, and a haunted forest trail that leads thrill seekers deep into the dark woods!

Of course, in between all these Annapolis activities, you can spend your time shopping, exploring historic Annapolis, and dining at any or all of the restaurants we are about to tempt you with below!

Annapolis Activities

Cafes, Diners, and Fancy Restaurants

Your dining options are numerous in Annapolis, no matter what season you visit, and the ones we are about to discuss are just a few of our favorites. We love to start our lazy Saturday mornings with the hardy breakfasts offered at the Iron Rooster-Annapolis. Located in Ego Alley, just a short walk from the unofficial parade of boats, you can walk off the extra calories from their crab and hash or shrimp and grits and enjoy a show at the same time! Galway Bay Irish Restaurant & Pub offers a great midday spot for pub food, Irish specialties, and refreshing beverages, and if you find yourself having such a great time you don’t want to leave, that is ok; you can always pick up with your Annapolis adventures another day! In business for nearly 25 years, the staff at Galway Bay are friendly, knowledgeable, and their cooks definitely know their way around the kitchen. Because crab cakes are a Maryland specialty, we seriously recommend Miss Peggy’s version!

When the dinner bell rings, these next restaurants will fill the empty spots in your stomach as they feed the soul, with this first one filling your desire to see and be seen. At Home Annapolis has talked quite a bit about Harry Browne’s, and yes, its surf and turf menu and small plates dishes are as delicious as they are innovative and hearty, but its their patrons that always impress! Located right across the street from the Maryland State House, this is the restaurant where VIPs love to dine, and on any given night you may run across a senator sipping brandy or a congressman enjoying a crab cake and corn fritters meal! Pusser’s Caribbean Grille is a popular restaurant option, offering waterfront views and delicious Caribbean specialties, including their famous surf & turf and a creamy and tangy key lime pie. When you are craving thick and juicy burgers, meatloaf like mom used to make, and big plates of crab nachos, a visit to the Double T Diner is up to the challenge of satisfying your comfort food appetite! Dessert is served at Red Bean, a coffee shop that also serves up your favorite ice cream dishes, but pretty much every restaurant listed above offers a delicious dessert menu, so you don’t have to make a special trip to sate your sweet tooth—unless you absolutely want to!

Choose Your Season and Choose At Home Annapolis!

Every Annapolis adventure is more exciting when you get to come home to At Home Annapolis, where comfort rules and style is never an afterthought! Our attention to detail and our desire to please are traits that make our homes the most desired vacation rentals in town. Reserve your favorite seasonal sanctuary today and discover a vacation experience you will wish never had to end. We hope to see you soon!