- © 2026 Annapolis Home Magazine
- All Rights Reserved
by Christine Fillat
We know you will enjoy all the fun day trips we propose that you try in the year to come. You’ll be picking peaches, fly fishing, hiking, and touring a grand estate. Many of these experiences require reservations or have specific requirements, such as proper attire, or tips concerning parking or availability of food and refreshments. Be sure to check their websites well in advance so you are prepared to fully enjoy these adventures.
Every Tuesday evening, Chronic Sailing offers free live music on Back Creek featuring acts such as Jimi Haha, Skribe, Callum, and Jordan Sokel. This unique concert series is accessible by kayak, paddleboard, or private boat; you may also attend on land, where it is visible from Helen Moyer Park. And did I say it’s free? It’s totally free!
For details, visit chronicsailing.com/tunesday
The Wednesday night racing program, sponsored by the Annapolis Yacht Club, is a true Annapolis tradition. Among the wonderful options to watch the race, you could join the Annapolis Maritime Museum on their graceful skipjack, the Wilma Lee, for a race day watch party.
For details, visit amaritime.org
Or…
Grab a table near the window of the Chart House and watch the sailors, under full sail, finesse their way to race across the finish line.
Or…
You could always stand on the Spa Creek Bridge and watch the drama. Races begin around 6:40 pm.
For details, visit www.annapolisyc.com
Feeling peachy? Hey! It’s peachy weather! Pick a peach! At Larriland Farm in Howard County, you can pick your fill of peaches and lots of other fruit, too: blackberries, blueberries, apples, and grapes.
For details, visit www.pickyourown.com
Probably the loveliest place to hang out and listen to the easy-going sounds of bluegrass: in Sandy Point Park, right on the Chesapeake Bay. Bring your chairs, bring your bathing suits, bring your Ma and Pa. September 19 and 20.
For details, visit baygrassfestival.com
Annapolis Rocks is a 7.1-mile hike along the Appalachian Trail in Maryland. Visit the All Trails website before you tackle this trek.
For details, visit www.alltrails.com/trail/us/maryland/black-rock-via-the-appalachian-trail
This year is the 55th annual Waterfowl Festival in Easton, Maryland! While anything related to waterfowl and hunting is at the fore, there is something for everyone here: duck carving demonstrations, artwork, food, clothing for sale, and live music. The Dock Dog competition is a big treat: watch as all sorts of dogs launch themselves into the air before splashing down into a swimming pool for the sheer joy of it. The dog that travels the farthest distance gets a prize! November 13-15, 2026.
For details, visit waterfowlfestival.org
Alfred Barnes amassed an eclectic and valuable art collection between 1912 and 1951, including Impressionist paintings, African art, Native American artifacts, Pennsylvania Dutch furniture, Greek antiquities, and decorative ironwork. In his museum, he arranged these objects according to how he felt they related to each other. Visit this Philadelphia museum to decipher the genius of Barnes’ sensibility.
For details, visit www.barnesfoundation.org
If you want to get closer to our feathered friends, consider visiting the Maryland School of Falconry in Reisterstown, Maryland. Learn all about falcons and actually get the opportunity to wear the leather glove and hold one of these majestic creatures. Reservations required.
For details, visit marylandschooloffalconry.com
Visit Washington, D.C.’s Chinatown for the Chinese Lunar New Year, celebrating 2027: The Year of the Fire Goat. It begins on February 6 and runs throughout the month with a parade, Smithsonian museum events, and terrific food.
For details, visit washington.org
The Glenstone is a museum that takes your breath away. The number of patrons visiting at any time is controlled, giving the viewer a sense of being on a private tour of this stunning collection of post-WWII art. The architecture of the interior galleries, carefully considered, is rendered in subtle shades of grey. Strike up a conversation with any of the grey-clad docents in each gallery—that’s what they are there for! A raised boardwalk through the forest grounds takes you past various installations and gardens. This is an elevated multi-sensory experience; take your time and enjoy.
For details, visit www.glenstone.org
Visit Hillwood Mansion in Washington, D.C. Businesswoman and philanthropist Marjorie Merriweather Post lived here from 1955 until she died in 1973. These gardens were an integral part of Post’s daily life and lavish social scene. Her gardens were designed to feature spectacular springtime displays of thousands of tulips, slipper orchids, flowering trees, and bushes. Tour the gardens or participate in a walk with a certified forest bathing guide.
For details, visit hillwoodmuseum.org
Any fan of the Paramount television series The Madison or the film A River Runs Through It will admit to having a keen desire to learn how to fly fish. Blame it on the gorgeous landscape, the tranquility of being on the water, and the possibility of actually nabbing a lovely fish.
Orvis offers a fly-fishing school in Stevensville, schools@orvis.com.
Tight Lining is a fly-fishing school based in Bel Air, MD, with classes hosted by Mike Slepesky, mike@tightlining.com.
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The Faces of Annapolis 2026