Things to Do for Halloween in Annapolis

When it comes time to start planning your Halloween escape to our favorite city on the Bay, you may be wondering what exactly there is to do in one of our nation’s oldest towns. Annapolis is known for the US Naval Academy, the Chesapeake Bay, and for being the sailing capital of the world, but it can also be an exciting place to spend Halloween and when you choose our At Home Annapolis holiday hideaways for your vacation accommodations, well, your getaway for Halloween in Annapolis will be about as perfect as one can get!

Londontowne Symphony Orchestra: Halloween Spooktacular, October 17, Maryland Hall

Halloween is different from most other holidays, celebrating what scares you and reveling in the weird, and music helps set the mood. The Londontowne Symphony Orchestra provides the perfect soundtrack to be frightened by, playing songs from some of your favorite Disney movies, adding spooky sounds and a costume contest to create the best Halloween celebration ever!

Annapolis, Maryland Bewitching Soiree, October 19, Cooper’s Hawk Winery & Restaurant

Not every Halloween vacationer travels with kids and when you are looking for a grown-up way to party, Cooper’s Hawk Winery & Restaurant has the perfect way to do so with their Bewitching Soiree. Offering a night filled with haute cuisine holiday themed dinners, paired with silky wines, and a Dark Cocktail greet to start the event, they encourage participants to wear something black to go along with the theme. Spend an evening sipping and sampling with the adults and then come home to the comforts of our At Home Annapolis getaway to ensure this night is one you will never forget!

Halloween Party and Parade, October 30, Whoof on the Wharf in Edgewater

Located approximately 6 miles from your At Home Annapolis escape, the Halloween party and parade sponsored by Whoof on the Wharf promises to be unlike any other you have ever experienced. Where else can you witness a parade of witches, werewolves, and other spooky creatures paddling away on the South River? Offering a costume contest, professional photos, and a plethora of four legged fur babies determined to charm their way into your heart, this fun event promises to be the highlight of your Annapolis Halloween journey!

Ghost Walks, Sweet Treats, and More This Halloween in Annapolis

The haunts keep on coming during your Annapolis vacation, offering Ghost Tours from Annapolis Ghost Tours & Crawls, sweet treats with a Halloween theme from Sweet Hearts Patisserie, and so much more you will wish your visit never had to end! Reserve your favorite holiday hideaway from At Home Annapolis today!

Our Favorite Fall Activities in Annapolis

Every season is the perfect season for a getaway to Annapolis, but we have to admit that fall holds a special place in our hearts. Offering cool days after a summer of heat and humidity, trees that are ablaze with all our favorite colors, and the scent of fireplaces being used for the first time since the spring wafting through the air, there is no downside to fall in Annapolis, with one exception: Eventually, the season has to end! This guide to our favorite fall activities in our favorite town on the bay will help make your autumn adventures memorable ones.

Savor the Flavors of Fall With These Activities in Annapolis

Yes, fall is known as the season of pumpkin spice, but a sip of hot cocoa from the Annapolis Ice Cream Company will forever change that in your mind! Rich, thick, and creamy and also voted “The best hot chocolate in Annapolis,” every sip will be your favorite, warming you from the inside out. And because outside is where you will want to be during this season of wonder, why not take a cup to go and walk out to City Dock? Watching the boats come and go on the sometimes stormy, most often placid waters of Chesapeake Bay against a backdrop of trees offering canopies of fire is a time-honored fall tradition that should definitely be added to your itinerary of activities in Annapolis.

West Annapolis Oktoberfest, September 26th

As the pandemic loosens its grip ever so slightly, more festivals and events are making a reappearance on the Annapolis calendar, and that includes our favorite fall celebration, West Annapolis Oktoberfest! Offering food, beverages, entertainment, and a little shopping, this ode to October never fails to be a good time. If you go, please be sure to raise a beer in toast to the joy our bayside city is bringing you! If you find a pumpkin porter, you won’t be cheating on the hot chocolate you enjoyed earlier; when alcohol is involved, it is a totally different category!

Annapolis Ghost Tours and Haunted Pub Crawls

When you’re looking for a spooktacularly great time, look no further than the streets of Annapolis and the Ghost Tours and Haunted Pub Crawls offered there! Available again, you can learn about the scary underbelly of our historic town with true stories told by knowledgeable guides or drink where the heroes of our nation once drank and hear more stories of the spirits who still make their presence known.

Fall in Love with Fall with At Home Annapolis

Designed to comfort and spoil, our seasonal sanctuaries will warm your hearts and speak to your soul. Reserve yours today!

Property Walkthrough: Whimsy in Wardour

If you have ever thought there just isn’t enough whimsy and wonder in your everyday life, we can change all that when you choose our 5-bedroom, 3.5-bath Whimsy in Wardour sanctuary for your vacation accommodations! Bright, airy, and spacious enough to hold 10 people, this sweet space might just be one of our favorites. We just can’t wait to show it off, so keep reading to get a hint at how the seven days of your vacation can end up being the most comfortable ones in recent memory!

If Comfort Had a Proper Name

Comfort is a word that evokes images of over stuffed sofas, soft beds topped with silky linens, and hugs from our favorite people, and if the word had a proper name, we believe that name would be Whimsy in Wardour! Drive up the curved driveway and be charmed by flowering bushes and well-groomed trees that surround the home, and as the big red door swings open, your gasp of happiness won’t be contained. Inside, wood floors lead the way to the living room, a welcoming and inviting space offering plush sofas, a classic fireplace, and for a touch of whimsy, a ship in a glass case serving as a nod to the fishermen who make our favorite city on the bay their home. This isn’t the only living space, however, making this the perfect home for those traveling with multiple families; a sunroom, a basement sitting area, and all kinds of seating areas outside all work together to create a simple paradise you will love! The kitchen is bright and cheerful, featuring a large center island topped with granite with four chairs surrounding it, stainless steel appliances, and updated appliances you won’t be able to wait to get your hands on. Fitness equipment will keep you in shape as you devour meals filled with extra fat and calories, a pool table is where you can show off your inner hustler on a rainy Tuesday, and when the sun shines bright and the temperatures rise, outside, a screened-in patio provides safe shelter from insects and a clear blue swimming pool provides hours of cool entertainment! The tour of this sweet shelter continues back inside, with each room offering the perfect place to retreat to after a long day of exciting vacation adventures.

No End to the Fun in This Annapolis Vacation Rental

Every inch of Whimsy in Wardour is built to be enjoyed, so don’t waste another minute! Click that book now and start planning your unforgettable Annapolis getaway in our Annapolis vacation rental!

Rainy Day Activities in Annapolis

When you first arrive in Annapolis you may be awed by the all the green that is a big part of the natural landscape. From the trees to the meadows, our town offers a lush landscape of beauty, into which a little (or a lot) of rain must fall. If the rain falls during your once in a lifetime Maryland vacation, do not worry that your trip will be ruined; instead, discover all these rainy day activities in Annapolis that you might have missed out on if the weather had stayed dry and clear! This guide will introduce you to the inside wonders that make Annapolis a town you will never want to leave.

Savor the Past With These Activities in Annapolis

Our city on the bay played a huge part in the development of our young nation, and as you might expect, a lot of that history can be studied today as you visit the museums that honor the past! From the Annapolis Maritime Museum that studies the lives of the seafaring people who built our town to the structures that were once homes to the bravest of all men, the signers of the Declaration of Independence, including the William Paca House and Garden, the rain can soak the streets and raise the levels of the Severn River, but you will stay warm and dry, losing yourself in history!

Renew Your Love Affair with Shopping

The pandemic put a damper on our shopping habits, but a little rain will never dampen your enthusiasm over a great shopping trip, and the boutiques, shops, and stores of Annapolis hold all the merchandise you never knew you needed! Celebrate Christmas year-round with a visit to A Christmas to Remember (172 Main Street), pick yourself up a little rainy day surprise at AL Goodies General Store (112 Main Street), or treat your sweet tooth with a something sugary from Uncle Bob’s Fudge Shop and keep your disposition sweet no matter how hard the rain falls!

Savor the Moments

During most of your vacation, chances are you have been rushing from place to place, trying to see and do it all in a short amount of time. The rain can act as a message from Mother Nature, telling you to slow down and savor the moments spent with family. A rainy day is the perfect time to stay “home” and enjoy the comfort and luxury amenities found in our At Home Annapolis sanctuaries—reserve yours today!

Top Tours to Experience in Annapolis

Now that you have figured out the easy parts of your upcoming vacation, including choosing Annapolis for your destination and At Home Annapolis for your accommodations, things can become a little more unclear when it comes to the other details, especially if this is your first time visiting our beautiful city on the Chesapeake Bay. Fortunately, your early choices have led you to us, and we want to make sure you enjoy every minute of your getaway. As such, we are providing this guide to the top tours in Annapolis to experience during your stay!

Annapolis Trolley, 2404 Nichols Road

Trolley tours are generally the best way to get to know the place you are visiting, giving visitors the opportunity to catch a glimpse of the places that most interest them, learn their history, and perhaps decide to come back at a later time to explore in more depth! Annapolis Trolley offers a series of Discover Annapolis tours that will give you the inside scoop on what makes our town tick. The red trolleys are comfortable, fun, and make a great backdrop to family pics, so don’t forget to bring your camera!

Food Tours in Annapolis

The best way to get to know any town is by sampling the cuisine for which it is known, and Annapolis Food Tours offers a Best of Annapolis tour that does just that. Lasting 3.5 hours and taking guests to some of the best restaurants in town, each offering a dish for which they are famous, the history lesson that accompanies the tour is fascinating! Offering more than just a taste of the town, this food tour also takes guests past some of the more historic spots in town, so be sure to make the tour one of the first you take.

Watermark Tours, 1 Dock Street

As you may have suggested by the name, this awesome tour company offers a variety of water tours guaranteed to impress even the most cynical of travelers! Cruise the bay with a tour lasting anywhere from 40 minutes to a full day on the Harbor Queen and be “swept away” by the beauty of the town, the bay, and if you are still on the cruise at sunset, the magnificent colors that light up the sky!

The Best Is Yet to Come

Each day will be filled with adventures you will never want to forget, and when you come home to your At Home Annapolis luxurious escape, the nights will be even better! Reserve your stay with us today!

Early Summer Activities in Annapolis

As the weather turns from cool to warm and the sun stays out later every evening, many travelers are deciding that this early summer period of beauty is the perfect time for a vacation getaway to Annapolis—and we would have to 100% agree! This time of year offers so many benefits, from less crowds to cooler temps, it may become your favorite time to travel. Our guide to all the fun you can have during your early summer getaway in Annapolis will ensure that every minute of your stay is filled with excitement, relaxation, and joy!

The Beauty of At Home Annapolis

Staying home with At Home Annapolis is an experience you will want to try again and again as you spend your hours really getting to know the comfort and luxury our homes offer. Rent a home with a pool and plan your own private pool party complete with cannonballs, hot dogs on the barbecue grill, and your favorite music enticing you to bust your best dance moves. Watch romantic movies on rainy nights accompanied by fresh popped popcorn and a glass of your favorite wine or wake up early to watch the sunrise over the bay, made easier in one of our waterfront homes. Everything you do in one of our At Home Annapolis summer escapes promises to be the highlight of your already spectacular getaway!

Venturing Out With Annapolis Activities

Of course, if you spent your entire vacation at home, you might be a little disappointed that you missed out on picnics you could have had at Quiet Waters Park, antique shopping on the “Vintage Loop,” or the simple pleasures found in an ice cream cone from Storm Brothers Ice Cream Factory. Walking along cobbled streets while exploring the historic district, visiting homes of signers of the Declaration of Independence or examining, or taking a tour of the world-famous Chesapeake Bay, followed by crab cakes at O’Leary’s Seafood Restaurant, are all activities that hold great charm with visitors and residents alike. If you came all this way without at least attempting a few of the items we have listed here, your trip would not have been as stellar as you had hoped! Our city on the bay is made for adventures big and small, and we encourage you to explore everything there is to do when you embark on a day of Annapolis activities.

Book Your Summer Stay Today

Knowing you will be coming home at the end of each adventure to the comforts of our special properties will make the separation anxiety a little easier to bear. Reserve your summer stay today!

Most Romantic Activities for a Valentine’s Getaway in Annapolis

Although we really should be showing the loves of our lives how much we appreciate them every day, generally we save the romance for two or three days out of the year—birthdays, Mothers or Father’s Day, anniversaries, and of course, Valentine’s Day! And because this year we are all still feeling off balance and out of whack, we suggest you go the extra step and whisk your Valentine away for a special holiday weekend in historic Annapolis. If you really want to spoil her, choosing At Home Annapolis will bring your romantic getaway to the next level of wonderful!

Sweets for Your Sweetie

The allure of an excellent piece of chocolate can not be underrated, and the Chocolate Moonshine Company at located at 1730 Annapolis Mall Road shows us something we have all been missing! Whether you are stopping by on your way into town for some romantic activities in Annapolis or preparing to slyly slide a selection under her pillow or are including the shop in your shopping adventures (allowing her to pick the pieces she loves most), the chocolate offered here will sweeten your time away! The 4-pack Artisan Bars pre-built collection is one of our favorites, but every candy found at the Chocolate Moonshine Company is guaranteed to please!

Binge on Romantic Movies

Couples with children often forget what it is like to be along together, so it doesn’t surprise us that many of our guests choose to spend at least one day of their Annapolis visit staying and exploring the charms our At Home Annapolis love nests have to offer. Starting with breakfast in bed (our kitchens make cooking fun again) and ending with a romantic movie binge-a-thon on state-of-the-art televisions that make you feel as if you are a part of the movie, this Valentine’s Day will be the one you both remember forever!

A Night on the Town With These Romantic Activities in Annapolis

Not all parents want to spend another night staying in, especially during their Maryland getaway! Valentine’s Day is on a Sunday this year, but there’s no rule that says you have to wait until the 14th to celebrate; Saturday nights in Annapolis can be exciting adventures that you never want to end! Share a bottle of wine in the romantic atmosphere offered by Red, Red, Wine Bar (189 B Main Street), see and be seen at Harry Browne’s at dinner (66 State Circle), and finish off the evening with music and more drinks at Rams Head Roadhouse (1773 Generals Highway). However you spend your days and evenings in Annapolis, spending your nights in one of our cozy and romantic At Home Annapolis hideaways will be the best decision you have made this year. Reserve yours today!

Isolated Activities in Annapolis

As travel restrictions are being lifted and we begin to start roaming around the country again, we are all still feeling a bit cautious as we maintain the perfect social distance and wear masks every time we step out our doors. But how do we social distance when we are visiting places that are known to be tourist hot spots? The Vietnam Memorial in DC, the Grand Canyon in Arizona, and the US Naval Academy, located right here in our hometown of Annapolis, are all tourist magnets and therefore should probably be removed from our bucket lists for the time being, but that doesn’t mean you should give up your exciting getaway to Annapolis altogether. During these troubled times, we all deserve a little something special, and this guide to isolated activities in Annapolis you can enjoy during your stay in our city on the bay will ensure that this vacation will be fun and safe!

Stop and Smell the Flowers

Our souls are hungry for peace and serenity, something you can easily find in the Tawes Garden & Arboretum, located at 580 Taylor Avenue. Helen Avalynne Tawes was the wife of one of our former governors and her love of horticulture is clearly apparent across 5 acres of land designed to showcase the beauty of our natural landscape. Although you may run into a few people while you are exploring, if you follow the directional signs, follow social distancing guidelines, and avoid traveling in groups of 10 or more, peace, serenity, and safety will be yours!

A Walk in the Park

It’s the quiet moments that often offer the greatest impact, and a walk in the Quiet Waters Park on Hillsmere Drive can become the highlight of your getaway. Hike along the 6 miles of trails, all paved, making them simple to navigate for people with physical issues, or rent a kayak and social distance from the middle of the South River that runs through the park.

Stay at Home with At Home Annapolis

Finally, when you choose to take a day or so and spend it at home in your At Home Annapolis vacation escape, you’ll truly understand why you chose us. Offering a quiet luxury that doesn’t need to be shared with the rest of the world, our homes offer many features you won’t want to live without, including private pools and large yards, game rooms and hot tubs, and a welcoming warmth that will remind you of your own home. Reserve yours today!

Water Activities to Enjoy in Annapolis

Every vacation is special, but there is something so wonderfully extra about a waterside getaway. As you fill the minutes of your all too short getaway with boating adventures and cannonball competitions, you realize that these moments are as close to perfect as they can be! When your vacation journey brings you to Annapolis and the world-famous Chesapeake Bay, you have to know that it’s going to be even better— especially when you choose At Home Annapolis for your comfy hideaway! This guide to water activities in the area will ensure that you don’t miss out on a single second of fun.

Ahoy There, Mateys!

Life aboard a pirate ship has never been this fun—probably because the real pirates didn’t have Pirate Adventures planning their trips! Board the Sea Gypsy for a few hours of fun that allows your children to experience life on the seas. Dress like a pirate, discover a message in a bottle that leads your young scalawag to the “most rotten pirate on earth,” and defeat said pirate with a real-life battle that involves water cannons and a sunken treasure. This adventure will prove to your children once and for all that you really ARE the best parents on earth!

The Wind Beneath Your Sails

Annapolis is considered the sailing capital of the United States, so it would definitely be remiss of you not to partake of a sailing adventure. Annapolis Sailing Cruises offers one of the best sunset sailing cruises in the world, and we invite you to check it out! Feeling the wind beneath the sails of the Woodwind (or Woodwind II) as the sun sets over the bay is an experience you will never forget, and if you share it with the one you love, this will be one adventure that brings you closer together. A cash bar stocked with wine and beer amps up the experience to the next level!

Great Water Activities and Beautiful Waterfront Living

The best way to enjoy all the wonders of the bay is by choosing one of our At Home Annapolis waterfront escapes! And whether you are sitting on the pier outside your abode with fishing pole in hand and earbuds playing your favorite tunes or have chosen to do your best cannonball into the waters beneath the dock, your days of Maryland fun will be some of the best ones in your life, especially when sitting in a hot tub on the deck as the lights from billions of stars glow brightly in the night sky. Reserve your At Home Annapolis waterfront escape today!

Enjoy Great Outdoor Activities in Annapolis

Whatever season you decide to take your Annapolis journey, you can be assured of one thing: Spending as much time outside as possible is going to be your favorite thing to do! After weeks of self-quarantine, being able to break free of the “chains” that bound you to your home is a gift you will appreciate for years to come! This guide to all of the outdoor fun you can have with these activities in Annapolis during your Maryland getaway will ensure every minute of your trip will be filled with excitement and exploration. And when you choose At Home Annapolis for your vacation accommodations, your evenings and nights will be equally delightful!

Take a Hike

It doesn’t matter how long the hike or how short the walk, wherever you explore on foot in Annapolis, you’re going to fall in love. Our city on the bay is blessed to be home to over 80 trails that will take you to some of the most beautiful spots in Annapolis. From the Jonas Green Park Trail with its wide paved paths and flourishing gardens to the moderately rugged ones in Broad Creek Park, there’s beauty to be discovered everywhere you look.

The Trolley Tours is One of the Great Activities in Annapolis

The trolley tours of Annapolis are some of the most popular attractions in town, giving guests the opportunity to catch a glimpse of the most special spots before diving in to explore the ones they most appreciate. Discover Annapolis Tours offers two tours, one that lasts 60 minutes and another that stops at only 40 and includes stops at the Annapolis City Dock, drives past some colonial mansions, and plenty of peeks at the scenic views of Chesapeake Bay.

Sail Away

When you live near the water, you can expect that most popular activities would revolve around the it. Sailing is big in Annapolis, and in addition to being the home to one of the biggest sailboat shows in the country, we also offer sailboat cruises and sailing lessons for your outdoor enjoyment! Schooner Woodwind Sailing Cruises offers a variety of cruises, including the most romantic of all, the sunset cruise! Annapolis Sailing School gives you the tools to be able to sail any time you like!

Stay Home and Play

On those days you just don’t feel like getting out of your comfy clothes, staying home for a day and exploring the amenities in your At Home Annapolis vacation escape will sound like the most excellent of ideas, especially if you choose one of our properties with a pool! Sunning yourself, reading, or practicing your cannon ball has never been this fun. Contact us and reserve one of our luxury properties today!