Why the Idyllic Eastern Shore Town of St. Michaels Should Be Your Next Weekend Getaway

The quaint, bustling Eastern Shore town of St. Michael’s has a lot to offer and is the perfect weekend getaway for those seeking some R&R. Located off the Eastern Bay and Miles River, St. Michaels dates back to the mid-1600s when it served as a trading post for area tobacco farmers and trappers. The town still reflects its colonial past with its many preserved historic homes dating from the late 1700s and 1800s. Whether you’re looking for historical charm or nautical adventure, St. Michael’s is the place to be. Here’s our suggested day itinerary, whether you plan to stay for either the day or an extended weekend trip in one of the many charming inns.

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What To Do

1. Explore the historic downtown’s Talbot Road. Wander into whichever stores look interesting for fun oddities, apparel, and art, then get a coffee and pastry at the Blue Crab tucked just behind the main street to keep you fueled.

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2. Stroll around historic neighborhoods. We swear, simply strolling around the picturesque town is an art form here – especially when you have to also pay attention to the uneven brick sidewalks. Once you’re finished meandering Talbot Road, pop down the side streets to admire the historic and beautiful homes. If you’re interested in learning more about the building’s histories, the St. Michaels Museum put together this helpful guide.

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3. Walk down Cherry Street and cross Honeymoon Bridge towards the pier. The bridge has connected the foot of Cherry Street to Navy Point for pedestrians since the late 19th century when the first summer guest cottages opened along the Navy Point waterfront. From the small foot bridge, you’ll spot the Museum’s Hooper Strait Lighthouse straight ahead. The bridge is a worthwhile stop for a quick photo.

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4. The Chesapeake Bay Maritime Museum is home to a collection of Chesapeake Bay artifacts, exhibits, and vessels. The 18-acre interactive museum is located on the water at the site of former seafood packing houses, docks, and work boats, plus the Hooper Strait Lighthouse dating from 1879. Come in the late afternoon for fewer crowds and a gorgeous view of sunset over the bay.

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5. Muskrat Park is a cute little park off the water and close to the main street shops. Sit and enjoy the view.

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6. Get out on the water and take a boat ride or kayak to enjoy the water and get a different perspective of the town.

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7. Christ Church Episcopal and Union Methodist Church are both unique and historic structures. Plus, you may spot some of the local families’ headstones at the Christ Church graveyard – pay attention, and you’ll notice these names come up over and over again.

8.Sample local beer and wine at Eastern Shore Brewing and St. Michaels Winery. Located right in town and across the street from one another, you hardly have to move to get a taste of these popular local watering holes.

Where To Eat

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The Blue Crab Coffee Co. – a sweet local gem tucked right off the main street. Erected in 1883 and former home of the Freedom’s Friend Lodge of Odd Fellows, the building is now home to a coffee shop serving up delicious coffee, espresso and tea drinks plus a café style menu with quality ingredients. Rest your feet and sip coffee while playing board games located in the back.

Foxy’s Harbor Grill – slightly elevated bar style food inspired by the mid-Atlantic with a great view of the bay. Watch boats pull up and dock as you enjoy the fresh breeze coming off the water. Try the crab pretzel and crab sandwich, and don’t forget to cool down with a tasty cocktail. Dog friendly.

Ava’z Pizzeria & Wine Bar – Spot with fantastic pizza (we do not claim this lightly) with a solid beer list. If there’s a wait, we promise it will be worth it. Check out their creative beer tap fountain on the twinkly light back patio.

Bistro St. Michaels – New American restaurant with a fresh menu sure to satisfy everyone’s taste buds.

Limoncello Restaurant & Wine Bar – Charming bistro serving up very good Italian fare with wonderful service. Ideal for a special date-night spot.

The Inn at Perry Cabin – The restaurant at this tucked away resort is impeccable. Enjoy the outdoor patio tucked into beautiful landscaping under shaded awnings. Plus the entire grounds are absolutely stunning.


Looking for a place to stay? We’ve personally stayed at Wade’s Point Inn On the Bay and couldn’t recommend it highly enough. Think beautifully decorated rooms in a historic structure (our room even had a claw foot tub) with picturesque views of the bay and super friendly staff. Check out photos from our stay below!

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How to Spend 3 Days in New Orleans

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New Orleans: where history and culture come together to create a vibrant, dynamic city. Follow your NOLA, and let adventure find you! We promise fun discoveries are waiting around practically every corner.

Day 1

French Quarter & Bourbon Street

Roam the French Quarter by day, and you’ll be rewarded with exciting sights. Talented street musicians serenade passersby, and historic European-styled buildings lining the avenues will transport you to a faraway time. History is available for purchase at dozens of antique shops. Don’t forget to make a pit stop to fuel up on beignets at the charming Cafe Beignet or world-famous Café du Monde (open 24 hours, so you can stop in no matter when the craving hits). Near the waterfront, St. Louis Cathedral dominates the view of Jackson Square by day, and fortune tellers line the Square by night.

Those looking for a raucous night will enjoy bar hopping along the infamous Bourbon Street. Bars line the street and offer to-go drinks in plastic cups, which is totally fine in NOLA since open container is legal here. Go just one or two streets over on Royal St or Chartres St, and you’ll find yourself in a more tranquil, laid back atmosphere with jazz bars and unique dining options away from the more gaudy tourist traps.

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Bourbon Street by day

 

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Exploring  the French Quarter

Day 2

Garden District

Elegance is the definition of NOLA’s Garden District. Wander Charles Ave by foot, bike, or trolly past antebellum mansions and pristine gardens that line the boulevard. Lafayette Cemetery No. 1 is a popular attraction of the area with raised tombs in family crypts dating back to 1833. Saint Charles Ave and Magazine Street run parallel to each other on the outer edges of the Garden District and offer good dining and shopping options. Also, if you’re fortunate to visit New Orleans during Mardi Gras, this is a great, low-key area to catch city-wide and local parades! Plus residents go all out and dress up their homes in full theme: yellow, green, and purple.

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Strolling Saint Charles Ave

 

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Historic homes in the Garden District

Day 3

Uptown, Carrollton & Magazine Street

Beautiful 19th century homes and small scale shops and cafes reinforce small town vibes in Uptown and Carrollton. The neighborhood has many stylish and eclectic stores and countless dining options. We got a good caffeine buzz after stopping in a few quaint coffee shops including Rue de la Course, which is set in a historic bank building.

Audubon Park

Audubon has a small city park meets Central Park feel. The paved trail loops around the central golf course for 1.8 miles beneath a shady canopy of moss-covered live oaks. Audubon Park is perfect spot to picnic and soak up some sun.

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Aubudon Park

Foodie Must Eats

Sylvain – Set in a renovated carriage house originally built in 1776, Sylvain offers fresh American fare. Sylvain is an ode to impeccable Southern cooking at its finest. We loved the gulf shrimp crudo and champagne & fries pairing. Try to hit the restaurant at an off hour since they seat on a first come, first served basis. If you do have to wait, Sylvain’s excellent bar makes the time pass quickly.

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Sylvain (sylvainnola.com)

Cavan – Starving and tired after a long day of exploring, we were thrilled to discover a mansion from 1880s converted into a dining room on the entry level and a bar on the second floor. Walking into the beautifully deteriorating mansion was like jumping back in time. We closed the place down sipping on cocktails after dinner upstairs and listening to the bartenders’ ghost stories. P.S. Do NOT skip dessert here–its 100% worth those extra calories!

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Cavan dining room (cavannola.com)

Maple Street Patisserie – We found this pastry shop by chance wandering around Uptown. Apparently it was voted Best Bakery in New Orleans, and we’re not second guessing. Their king cake was amazing, not to mention creamy eclairs, delectable petit fours, and a guava turnover that sent our taste buds for a spin.

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Maple Street Patisserie’s guava turnover

Looking for weekend getaway inspiration? Check out our guide to doing New York City in 48 hours.

Are you a self-proclaimed foodie? We’ve got you covered with all the best spots in Jackson Hole.

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