Dreaming of a Perfect Spring Boat Day in Annapolis…

This past January and February 2026 were among the coldest months on record for Annapolis in the past 50 years.  Even the first session of the popular winter Frostbite Sailing Series had to be cancelled due to cold temperatures and frozen waterways.  The local creeks were frozen solid for weeks and even the Chesapeake Bay was nearly completely frozen, with only a narrow passageway remaining for ships en route to and from the Port of Baltimore.  While the past 2 months have not exactly been ideal for boating, they certainly did have us longing for spring time, sunshine, and the warmer months.  We are usually eager to take Proud Mary for a spin on the first warm weather days.  One of our favorite spring itineraries is cruising up the Severn River and then back into Spa Creek and Ego Alley.  We love to dock at The Choptank for rooftop cocktails and take in the scenery of our beloved town.  Spring time always seems to make downtown Annapolis come alive with visitors and locals alike, whether it be folks on Main Street sporting their best green outfits for the St. Patrick’s Day Parade or college kids and alumni decked out in their Sunday best for the annual St. John’s College “Johnnies” vs. The Naval Academy Midshipmen “Middies” Croquet Match on the lawn of St. John’s College.  The spring legislative session, Maryland Day, school field trips, spring sports games at the Naval Academy, the Annapolis Spring Sailboat Show, May Day…Annapolis blooms in the early spring!  After a cocktail and a bite at The Choptank, we love to stroll up Main Street for a cone at Annapolis Ice Cream Company.  The traditional half of our family usually sticks to our favorite Mint Oreo, while the other half might try a more adventurous spring seasonal flavor such as Lucky Charms or Strawberry Cheesecake Swirl.  As we walk back down Main Street towards a golden sky and the glistening waters of Ego Alley, we can’t help but feel gratitude and joy for the beauty of our small town!  We’ll hold on to this spring dream for the next few weeks while the snow and ice thaw and we count down the days to Spring Boating Season!