Maryland is home to countless waterfront towns, each of which is delightfully charming in its own way, but only one town has been named as one of OnlyInYourState's Best Small Town Getaways For 2023. Located on the Chesapeake Bay, Saint Michaels, Maryland is the definition of a hidden gem. Situated just 80 miles from both Washington D.C. and Baltimore, Maryland, it is the perfect destination for anyone looking to get away for a Small Town Getaway. Offering new surprises at every turn, you'll love discovering the town's unique history, scrumptious restaurants, splendid shops, and wondrous water views during this curated two-day itinerary.

Do you love visiting and learning all about America's small towns? Take our interactive quiz to discover which Small Town Getaway you should take this year.

History Of Saint Michaels

Named after the Episcopal Parish established here in 1677, the church attracted settlers who were involved in shipbuilding and tobacco growing.

During the War of 1812, the area was home to as many as half-a-dozen shipbuilders, and in 1813, a fleet under the command of Admiral George Cockburn moved up the bay and targeted Saint Michaels due to the presence of a militia battery erected to defend the town and its shipyards.During the Battle of Saint Michaels, residents dimmed their lights and hung lanterns in the trees beyond the town so the British cannonballs would overshoot the town, ultimately sparing Saint Michaels of any major damage. This story gave Saint Michaels its nickname as “the town that fooled the British,” and you can find remnants of this history in the Saint Michaels Historic District.

Saint Michaels eventually became a hot spot for oystering and crabbing and, through the late 20th century, has transformed into a sailing and tourist haven.

Is Saint Michaels Worth Visiting?

Without a doubt, Saint Michaels is absolutely worth visiting.

This charming town is known for its picturesque scenery, rich maritime history, and friendly community. It’s also off-the-beaten-path, which makes for a low-key weekend away. Yet there are still plenty of things to do in St. Michaels.

How To Get To Saint Michaels

Located on Maryland’s Eastern Shore, Saint Michaels is approximately an hour from Annapolis, across the Chesapeake Bay Bridge.

The bridge backs up on popular holiday weekends, so time your drive across the bridge early in the morning or in the evening. Saint Michaels is also less than two hours from both Baltimore and Washington D.C., as well as 2.5 hours from Philadelphia. No matter where you live in this region, this is an easy spot for a weekend getaway.

Getting Around Saint Michaels

The best way to get around Saint Michaels, Maryland, is on foot.

You’ll find several public parking lots throughout the town, but they fill up quickly on the weekends. We suggest finding a spot to park, wearing comfortable walking shoes, and exploring the area on foot to discover countless charming boutiques, restaurants, historic homes, and more. There are also several walking and biking trails in the area, and bicycles are popular as well.

Best Time To Visit Saint Michaels

Saint Michaels is a haven for tourists during the warm summer months and that means that the beaches, restaurants, and hotels can get a bit crowded.

If you want to enjoy smaller crowds and more affordable rates, we suggest visiting right before or after peak season in May or September. Christmastime is also a popular time to visit, with its plentiful boutiques for shopping and even a dedicated Christmas store.

Where To Stay In Saint Michaels

Bed and breakfasts, inns, and boutique hotels are the stars of the show here in Saint Michaels.

There are several unique places to stay in Saint Michaels, Maryland, but we decided to visit on a whim, so our options were limited. I was so grateful we ended up at The Wildset because this boutique hotel was incredibly charming. Other popular options in Saint Michaels include the Inn at Perry Cabin and the Saint Michaels Harbour Inn.

Housed within three separate historic buildings that have been fully renovated, the aesthetic at the Wildset is immaculate. I took so many design ideas home with me and can’t wait to return.

In addition to the award-winning on-site restaurant, Ruse – reservations are strongly encouraged – The Wildset is home to The Sundry, a thoughtfully curated store and coffee shop in the lobby. On the back lawn, you will find lawn games as well as a firepit – with complimentary s’mores offered every night. We stopped by on our way home from dinner around 8 p.m., and there were several other families enjoying s’mores. Our daughter got to run around with other kids to let out some energy, and we got to relax and chit-chat with other hotel guests. It was absolute perfection.

Saint Michaels Getaway: Day One

Assuming you are driving from the areas between or near Washington D.C. and Baltimore, your drive to Saint Michaels will be less than two hours, and we estimate that you’ll arrive between 9 and 10 a.m. on day one.

Our morning will start with finding a parking spot and grabbing either breakfast, coffee, or both. Popular options include Skipjack’s, Eat Sprout, and The Blue Crab.

Day one is all about immersing yourself in the maritime history of Saint Michaels, so we will begin at the Chesapeake Bay Maritime Museum.

Home to a collection of Chesapeake Bay artifacts, exhibitions, and vessels, this 18-acre interactive museum on Navy Point was founded in 1965 and was once the site of seafood packing, houses, docks, and work boats.

You’ll also discover a variety of unique maritime history in the surrounding area as well – including historic homes, ships, and more.

The neighboring Hollis Park is home to a ship-themed playground, which my daughter loved.

After walking along the water and learning about this historic community, we’ll sit down for lunch at Foxy’s Harbor Grill.

This casual harborside spot features postcard-perfect views of the water, and our daughter loved watching the boats come in and out of the harbor. We tried their special, a chicken curry salad sandwich, and the yuca poutine, which was delicious.

Our afternoon will be spent enjoying the water.

Saint Michaels is known for its exceptional sailing opportunities, but if you don’t want to charter a sailboat, you can easily explore the bay by kayak. Rentals are available from Shore Pedal & Paddle, a company that rents kayaks and bicycles so tourists and locals alike can better explore this picturesque area.

Check-in and freshen up at your hotel – we recommended The Wildset above – and head to your dinner reservation at the hotel’s on-site restaurant, Ruse.

With an elevated yet inviting atmosphere and a sommelier-led wine program, you’ll love every element of this fine dining experience.

After dinner, grab a s’mores kit from the hotel lobby and head out back for a simple, nostalgic dessert.

Saint Michaels Getaway: Day Two

Coffee is a requirement to fuel up for the day ahead to enjoy more St. Michaels things to do, so it’s time to grab your fix from Blue Heron Coffee.

This low-key coffee shop features quirky decor and delicious iced chai lattes. We grabbed breakfast from our hotel, but there are several breakfast options in town as well, including The Galley Restaurant & Bar and Stars Restaurant.

Next up, it’s time for a leisurely stroll or bike ride along the Saint Michaels Nature Trail, which takes you off the main road and through the beauty of this Eastern Shore town.

Along the way, you’ll discover waterfront views and a charming covered bridge as well as several stunning homes.

Depending on the time of year you visit, you might prefer to swap this morning and afternoon, but in the summer, it makes the most sense to enjoy the outdoors before it gets too warm. If you don’t have bikes of your own to bring along or are traveling by airplane, there are a few places in town to rent bicycles – including The Wildset Hotel.

Now that we’ve worked up an appetite, Corah’s Corner is the place to be for a low-key meal.

The patio is large, and there is often live music on the weekends. I personally recommend the prickly pear margaritas and watermelon arugula salad.

A summer weekend getaway isn’t complete without ice cream, and Justine’s Ice Cream does not disappoint.

Located right across the street from Corah’s Corner, this is the perfect spot to enjoy dessert before an afternoon spent shopping.

No matter what you’re shopping for – or your budget – there are a ton of cute boutiques and shops to discover in St. Michaels, MD,

We personally loved Olde Town Candy Company, Pemberton Pharmacy, and The Preppy Redneck.

Last night’s dinner was upscale, so today, we’re keeping it a little more casual with Carpenter Street Saloon or Ava’s Pizzeria and Wine Bar.

No matter where you choose to dine, you can expect a scrumptious meal and friendly service to end your getaway in Saint Michaels.

Pro tip: the Maryland Transportation Authority recommends hitting the Chesapeake Bay Bridge before 8 a.m. or after 10 p.m.

So, tell us: have you ever visited the charming town of Saint Michaels, Maryland? What is your favorite small town in the Northeast United States for a weekend getaway? Tell us all about it in the comments, and be sure to check out all of our favorite Small Town Getaways.