The Showcase Magazine - Articles

Six Things to do on a Weekend Getaway to St. Michaels

by Ashley Casorio


Long vacations where you get to rest and unwind are amazing, however you don’t always need a two-week vacation to return to work on Monday feeling rejuvenated.  Short trips almost have the same effect as power naps: a quick repose can leave you feeling even more energized.  Pair a quick getaway with little travel time and you’ll be relaxing fast.


When you’re needing that getaway, consider heading down to Maryland’s Eastern Shore and spending a few days in St. Michaels, a quiet town on the Chesapeake that many are dubbing “the new Hamptons.”  Here are the top six things to do on your weekend getaway:


  1. Chesapeake Bay Maritime Museum

With its storied past, the Chesapeake Bay holds many secrets and the Chesapeake Bay Maritime Museum reveals them to you.  Taking you through the age of the steamboat all the way to modern times, there is much to learn.  The 35 buildings (ten of which are accessible by the public) are built on what was once docks and seafood packing houses, giving a truly historic feel. 


  1. Blue Crabs at Crab Claw

If you didn’t have blue crabs on your trip did you even go to Maryland?  Visit this landmark for some of the best crabs around and roll up your sleeves and prepare to get dirty!


  1. Sailboat Cruise on the Chesapeake

One of the biggest features and attractions of the whole area is no doubt the water.   There truly is no better way to see St. Michaels than from the Chesapeake.  Opt for a quick ride or a sunset sail, the choice is yours.  Bonus: depending on your cruise, you may even get to catch a glimpse of the Inn at Perry Cabin, the location for some of the filming of Wedding Crashers!


  1. Eastern Shore Brewing Company

Vacations don’t always have to be go go go.  Kick back at the Eastern Shore Brewing Company with some beers that are crafted from some of the finest ingredients by local craftsmen.  If you brought your pup along for the weekend, he/she is more than welcome to join in on the fun.  Stop by for live music and bring out the pints and water bowls!


  1. Michaels Bike Tour

After all that beer, you’re going to need to get out and do something active.  Stop by the local bike shop to pick up some wheels and a map.  Choose to head out with a plan or just bike the peninsula taking in all the beautiful water views.  TriCycle & Run ( will deliver bikes directly to you, making this excursion even easier no matter where you are staying.


  1. Sunset and an Orange Crush at Foxy’s Harbor Grille

End your trip with some of the best views and drinks in town!  Located on the Miles River, Foxy’s Harbor Grille is an easy stop for boaters and land lovers alike.  Pull up dockside or landside and grab a Foxy’s Crush which is made of vodka, fresh-squeezed juices, and topped with Sprite.  Just add the sunset and you just might feel like you’re in the Caribbean.


The beauty of living in New Jersey is that we have many states nearby that offer up many different things.  Take advantage of this the next time you’re looking for a quick jaunt away from your daily grind.  North, south, east, or west, you just might be surprised.


Ashley Casorio is the writer behind The Wandering Ash travel blog: Follow her on Instagram and Twitter @thewanderingash for photos and musings on her travels.