Spend the Perfect Labor Day Weekend in Annapolis

Whether it’s going on a shopping spree, indulging in local cuisine, or adventuring through downtown, Labor Day weekend in Annapolis has it all. We invite you to journey through this nautical city. Explore the immense charm and lively energy found in the attractions, culture, and many events hosted in the city. With captivating waterfront views, Annapolis Waterfront Hotel, Autograph Collection offers an array of unforgettable experiences to fill your long weekend.

Experience Annapolis Sailing

Immerse yourself in the sailing culture of Annapolis, where the beauty of the open waters beckons. With Schooner Woodwind you can go on a voyage around Chesapeake Bay. Feel the exhilaration as you lend a hand in hoisting the sails. If a leisurely pace suits you better, simply relax and bask in the breathtaking vistas that unfold before your eyes. From the intimacy of a private excursion to the lively camaraderie of a public voyage, there are options to suit everyone.

Enjoy Waterfront Dining

Don’t miss out on one of the best dockside dining restaurants in Annapolis — Pusser’s Caribbean Grille. Nestled right beside Annapolis Waterfront Hotel, this culinary gem offers the finest and freshest of Chesapeake seafood. Whether you choose to dine indoors or opt for outdoor seating, every moment promises to be enjoyable. To truly elevate your evening, don’t miss out on the world-renowned tropical drink, Pusser’s Painkiller.

Discover Downtown Annapolis

Prepare to be whisked away into the enchanting realm of Historic Annapolis, an area renowned for its captivating charm and pedestrian-friendly allure. Grab a cup of coffee and enjoy the picturesque streets, where a myriad of pottery, antiques, jewelry stores, and plenty of shopping options await. Visit the iconic Main Street, where restaurants, art, and nightlife add a glimmering sense of liveliness to the city. Finally, enjoy a leisurely walk, ending by City Dock, where boats cruise across the water for a relaxing sight.

Have Breakfast by the Bay

With scenic views of the harbor at Annapolis Waterfront Hotel, the tranquility within your hotel room makes it tempting to stay enveloped in its peaceful embrace. Let breakfast become a cherished ritual with our Bed and Breakfast by the Bay package. Enjoy a moment of rest and delicious dining before you set out to explore the wonders of Annapolis.

Explore Annapolis’s Music Scene

Prepare to be captivated by the music scene of Annapolis as you step into the legendary venue, Rams Head On Stage. This intimate music club exudes an enchanting atmosphere, playing host to a lineup of exceptional national talents all year round. This Labor Day weekend in Annapolis, you can move to the rhythm of Danny Burns Band on Friday night, Albert Bouchard’s Imaginos on Saturday, and as the weekend draws to a close, savor the lingering magic with Danger Bird: A Tribute to Neil Young on Sunday.

Dine Under the Stars

Step into a realm of pure charm and enchantment during the Dinner Under the Stars event series. The first block of West Street in downtown Annapolis transforms into a pedestrian-only haven on Saturday evenings. Allow yourself to be whisked away to the idyllic streets of France, Spain, or Italy as the ambiance is reminiscent of open-air cafes. Embrace the evening’s open air, where a world of local dining, live music, and art awaits your curious spirit.

First Sunday Arts Festivals

Indulge in a leisurely Sunday as you wander through the vibrant stands of the First Sunday Arts Festivals. Find yourself in the rich tapestry of creativity here. Local artists showcase their masterpieces in a myriad of forms, from paintings to photography and intricate sculptures. Embark on a serene Sunday adventure and collect cherished keepsakes of your trip to Annapolis along the way.

With a trip to Annapolis, you can enjoy an unforgettable Labor Day Weekend getaway with loved ones by your side. At Annapolis Waterfront Hotel, you’ll be placed at the center of it all, with a prime location and exceptional experiences to pair.