Fall Journey to Annapolis

As the leaves on the trees begin to change from green to brilliant shades of gold, orange, and crimson, visitors discover that summer isn’t the only good time to visit our historic city. Fall in Annapolis is a time of wonder and warm family moments. The days grow shorter, temperatures grow cooler, and the smell of pumpkin spice wafts through the air. It’s impossible for us to choose our favorite season, but from September through December, life is better in Annapolis, the Annapolis tourist attractions look better, and our guide to your fall journey promises to make this season and this vacation one you won’t want to end.

Day 1: Settling In

One of our favorite parts of any vacation is exploring the place we’re staying during our visit, and we envy you your opportunity to explore your At Home Annapolis escape for the first time. After a long day of travel, this first night is for picking your rooms, rummaging through cabinets, enjoying some family fun in Annapolis, and a savory pie from Rocco’s Pizzeria, a local fixture; after just one slice, Rocco’s is destined to be your new addiction!

Day 2: United States Sailboat Show

Living on the banks of Chesapeake Bay is something we never grow tired of, and many of our day-to-day activities are water related. The United States Sailboat Show, held every October (2019’s show will be held from the 10th to the 14th) is one such activity, celebrating the graceful vessels that sail in from all corners of the globe. Featuring the best of the old and the new, your fall journey to Annapolis would be incomplete if you didn’t purchase a ticket to this exciting show.

Day 3: Colorful Hikes- A Whole New Level Of Family Fun In Annapolis

We love to hike along the many trails of Annapolis in the fall when the already breathtaking scenery turns to a fiery brilliance that never ceases to stun. Your third day in town is the perfect time to do so yourself! The Historic Annapolis Ramble is an easy trail that takes you through 7.9 miles of the most beautiful scenery in town. If your fall journey is also a pet lover’s one, you’ll be pleased to learn this trail allows your leashed fur baby to accompany you.

Day 4: Explore History

Every season is the right one to enjoy a tour of our Maryland State House, one of the biggest Annapolis tourist attractions. Today, your fall journey is taking you its doorstep. This is the seat of American history and the oldest state house that is still in use, and the trees that grace its landscape will welcome you with a bright and colorful cheer. Inside, while some areas have been modernized, you will still see parts that have been unchanged since it was built in 1772. Click here and find out how you can tour the Maryland State House.

Day 5: Take a Walk with a Ghost

To be perfectly honest, you may not be walking with an actual ghost, but the Ghost Tours offered by Annapolis Ghost Tours somehow seem spookier when done in the fall. Period-dressed guides take you and your family to the spots where the spirit world mingles with the living world and tell the stories of tragedy and drama that have taken place over the centuries.

Day 6: Dinner and a Show

As your time in Annapolis nears its end, it’s important to finish this fall journey on a high note, and we can’t think of a better way to do so than with a romantic dinner at Lewne’s Steakhouse (401 Fourth Street) followed by a wonderful live show at the Maryland Theater for the Performing Arts. The quiet atmosphere and attentive waiters make your meal taste even better, and the quality performances offered by the theater will have you thinking about the show you just watched long after you return home to reality!

Day 7: Packing is Such Sweet Sorrow

Yes, the day you have been dreading since you first walked in the door of your At Home Annapolis vacation escape has arrived: It’s time to pack up your belongings and head back home. But it’s not too late to enjoy more of the luxury amenities and comfort that comes standard in our homes. Sharing a cup of coffee in your pajamas as you discuss the week’s adventures is one of the best ways to say goodbye. Click here and reserve your stay with us today. Make all of this a reality!

Best Places to Stay in Annapolis

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