Destination Main Streets

St. Michaels, Maryland

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Something pretty amazing happened early on the morning of August 10, 1813. The War of 1812 was raging between the U.S. and Britain, and the British were planning an attack on the seaport of St. Michaels, Maryland. Word got out and the town evacuated. All the lights in the area were extinquished except for lanterns placed in the trees away from town. The British fired their cannons upon what they thought was the town, but aiming for the lanterns, they completely missed their target.

It's a good thing the plan worked. If the British had succeeded, a lot would have been lost. St. Michaels was voted the eighth most romantic getaway by Coastal Living Magazine. And it's no wonder. With its quaint inns, shops, and restaurants this town on the banks of the Miles River has a lot to offer anyone traveling the Eastern Shore and Chesapeake country. Many of the stores reflect the town's nautical roots, but travelers will find a wide range of choices, including antiques, clothing boutiques, and specialty shops to serve the daytrippers from Washington and Baltimore and the recreational sailors making a stop in the town.

St. Michaels is located in Talbot County on Maryland's Eastern Shore on a peninsula jutting out into the Chesapeake Bay. The town's Main Street is Talbot Street, which is part of Maryland Route 33, the major highway leading through the area. St. Michaels is about 78 miles from Baltimore, Maryland, 80 miles from Washington, DC, and 123 miles from Philadelphia, Pennsylvania. Another nearby Main Street community is Easton, Maryland, which is only about 10 miles away.

Photo Gallery

Our tour of St. Michaels will start on the southern end of Talbot Street and continue heading north.  We'll actually be heading west along Maryland Route 33, which turns into Talbot Street as it passes through St. Michaels along its winding course along its peninsula that juts into the Chesapeake Bay.  Judging by the sign, this looks like a good place to start.
Our tour of St. Michaels will start on the southern end of Talbot Street and continue heading north. We'll actually be heading west along Maryland Route 33, which turns into Talbot Street as it passes through St. Michaels along its winding course along its peninsula that juts into the Chesapeake Bay. Judging by the sign, this looks like a good place to start.
Talbot Street is the town's Main Street.  We don't have to walk far on Talbot Street to see that the sign delivers what it promises.  We soon find two large buildings.  One is a winery and the other a microbrew.
Talbot Street is the town's Main Street. We don't have to walk far on Talbot Street to see that the sign delivers what it promises. We soon find two large buildings. One is a winery and the other a microbrew.
As we continue up Talbot Street, we encounter some well-kempt historic, residential houses.  We're not yet in the heart of downtown St. Michaels.  You can tell by the pumpkins on the front porch that these pictures were taken in the Fall.
As we continue up Talbot Street, we encounter some well-kempt historic, residential houses. We're not yet in the heart of downtown St. Michaels. You can tell by the pumpkins on the front porch that these pictures were taken in the Fall.
At the intersection of Talbot Street and the appropriately named Chew Avenue is this quaint cafe with a kitchy decor.
At the intersection of Talbot Street and the appropriately named Chew Avenue is this quaint cafe with a kitchy decor.
We continue heading north on Talbot Street.  Here's a shop selling bike and rowing gear.  The flat landscape is great for biking and the town sits right on the Miles River so you're not far from the water.
We continue heading north on Talbot Street. Here's a shop selling bike and rowing gear. The flat landscape is great for biking and the town sits right on the Miles River so you're not far from the water.
This is the Col. Joseph Kemp House.  It was built by Kemp, a War of 1812 hero in 1805 in the Georgian style.
This is the Col. Joseph Kemp House. It was built by Kemp, a War of 1812 hero in 1805 in the Georgian style.
A pair of houses now being used as antique shops.  You can see by the decorations that Halloween is right around the corner.
A pair of houses now being used as antique shops. You can see by the decorations that Halloween is right around the corner.
Across the street, is a gift shop with some funky merchandise out on the sidewalk.
Across the street, is a gift shop with some funky merchandise out on the sidewalk.
And then we look back across the street again at the houses that have been converted to shops, including this boutique here.
And then we look back across the street again at the houses that have been converted to shops, including this boutique here.
And we go back across the street again for a pizzeria-winebar.  Now that's an excellent combination.
And we go back across the street again for a pizzeria-winebar. Now that's an excellent combination.
We continue heading north on Talbot Street but here's a view looking back south the way we came at some shops and even a bistro we passed along the way.
We continue heading north on Talbot Street but here's a view looking back south the way we came at some shops and even a bistro we passed along the way.
The Old Brick Inn on the left is a boutique inn where you can stay right in the heart of St. Michaels.  It was the Wrightson Jones House named after a shipbuild in the War of 1812 who built the house around 1816.
The Old Brick Inn on the left is a boutique inn where you can stay right in the heart of St. Michaels. It was the Wrightson Jones House named after a shipbuild in the War of 1812 who built the house around 1816.
We look back across the street again at some more shops in St. Michaels.  Preppy Redneck is a clothing store whose name sums up the Eastern Shore lifestyle nicely.
We look back across the street again at some more shops in St. Michaels. Preppy Redneck is a clothing store whose name sums up the Eastern Shore lifestyle nicely.
Here's another view of that same row of shops.  On the right, is St. Luke's Methodist Church.  Members of the Auld family who owned Frederick Douglass are buried behind the church.
Here's another view of that same row of shops. On the right, is St. Luke's Methodist Church. Members of the Auld family who owned Frederick Douglass are buried behind the church.
At this point, we'll turn right and head east down Mulberry Street towards the water.  This is The Amelia Welby / Captain Wetheral House.  Captain Philip Wetheral owned the property in the area that was bought and developed into St. Michaels.  Amelia Welby who later lived in the house was considered the first Poet Laureate of Maryland.
At this point, we'll turn right and head east down Mulberry Street towards the water. This is The Amelia Welby / Captain Wetheral House. Captain Philip Wetheral owned the property in the area that was bought and developed into St. Michaels. Amelia Welby who later lived in the house was considered the first Poet Laureate of Maryland.
We make it down to the water where there's plenty of space to dock your boat.  There's also the St. Michaels Harbour Inn Marina & Spa.
We make it down to the water where there's plenty of space to dock your boat. There's also the St. Michaels Harbour Inn Marina & Spa.
Down by the water you'll also find more historic architecture and also restaurants with waterfront dining.
Down by the water you'll also find more historic architecture and also restaurants with waterfront dining.
The cannons along the waterfront remind visitors of the role that St. Michaels played during the War of 1812.  At one point when the British tried to bombard the town, the residents placed lanterns high up in the trees, causing the cannons to fire harmlessly over the town and miss almost all of the buildings in town.
The cannons along the waterfront remind visitors of the role that St. Michaels played during the War of 1812. At one point when the British tried to bombard the town, the residents placed lanterns high up in the trees, causing the cannons to fire harmlessly over the town and miss almost all of the buildings in town.
We come back up to the heart of St. Michaels on Talbot Street.  On the left is a Post Office and on the right is Mt. Pleasant, a former residence built around 1806.
We come back up to the heart of St. Michaels on Talbot Street. On the left is a Post Office and on the right is Mt. Pleasant, a former residence built around 1806.
More stores at the intersection of Talbot Street and Canton Street, including a clothing boutique and a Christmas shop.
More stores at the intersection of Talbot Street and Canton Street, including a clothing boutique and a Christmas shop.
Across the street is Christ Church.  The present church was built in 1878 but other churches had occupied this spot previously, including one believed to be dated back to 1677.
Across the street is Christ Church. The present church was built in 1878 but other churches had occupied this spot previously, including one believed to be dated back to 1677.
We look back across the street again and continue our northward movement through town.  Here we see some more shops.
We look back across the street again and continue our northward movement through town. Here we see some more shops.
Here's a block of colorful shops.  The one on the far left sells toys and games so those bright colors certainly fit.
Here's a block of colorful shops. The one on the far left sells toys and games so those bright colors certainly fit.
This is another view of that same row of stores.  You can see the Halloween themes in some of the merchandise being sold on the sidewalk.
This is another view of that same row of stores. You can see the Halloween themes in some of the merchandise being sold on the sidewalk.
Across the street, things are quieter, but that doesn't mean there aren't places to visit over there as well, including an Irish pub.
Across the street, things are quieter, but that doesn't mean there aren't places to visit over there as well, including an Irish pub.
Continuing north and going back across the street again, we come to the Town Hall Mall.  It was originally built in 1870 by the Masonic Company of Talbot County to be used as a Masonic Lodge and a Town Hall.  However, over the years, various owners have used the building for many purposes other than its original intentions and today it's a gift and home furnishings store.
Continuing north and going back across the street again, we come to the Town Hall Mall. It was originally built in 1870 by the Masonic Company of Talbot County to be used as a Masonic Lodge and a Town Hall. However, over the years, various owners have used the building for many purposes other than its original intentions and today it's a gift and home furnishings store.
Here's a view looking south back the way we came.  In the background, you can see the colorful shops we had visited a few pictures ago and in the foreground is a pharmacy that's also a gift shop.
Here's a view looking south back the way we came. In the background, you can see the colorful shops we had visited a few pictures ago and in the foreground is a pharmacy that's also a gift shop.
We continue heading north, but here's another view looking south.  The Town Hall Mall is on the right.
We continue heading north, but here's another view looking south. The Town Hall Mall is on the right.
Across the street is this row of shops and a restaurant at the intersection of Talbot Street and Carpenter Street that went all out for Halloween.  The American flag is out year round.
Across the street is this row of shops and a restaurant at the intersection of Talbot Street and Carpenter Street that went all out for Halloween. The American flag is out year round.
And going back across the street again is the supermarket.  For a large grocery store in the heart of town, at least it's pedestrian friendly without a huge parking lot breaking up the flow of foot traffic.
And going back across the street again is the supermarket. For a large grocery store in the heart of town, at least it's pedestrian friendly without a huge parking lot breaking up the flow of foot traffic.
Directly across from the supermarket is this row of shops.  The one on the left is interesting.  Although, it's a clothing boutique it almost looks like it could have been a fairly new house even with a driveway.
Directly across from the supermarket is this row of shops. The one on the left is interesting. Although, it's a clothing boutique it almost looks like it could have been a fairly new house even with a driveway.
We continue heading north and find some colorful boutiques decked out with some Victorian-style gingerbread.  This is a view looking southbound.
We continue heading north and find some colorful boutiques decked out with some Victorian-style gingerbread. This is a view looking southbound.
We turn around and face northbound now along Talbot Street.  You can take a break from the shopping to grab some ice cream.
We turn around and face northbound now along Talbot Street. You can take a break from the shopping to grab some ice cream.
Here's a view of the same stretch of businesses but this time from across the street.
Here's a view of the same stretch of businesses but this time from across the street.
At the intersection of Talbot Street and Railroad Avenue is this clothing outlet.  It looks small from this angle, but the store is pretty deep and is pretty large.
At the intersection of Talbot Street and Railroad Avenue is this clothing outlet. It looks small from this angle, but the store is pretty deep and is pretty large.
Across the street on the east side of Talbot Street is this sushi bar and grill.  The palm trees and thatch umbrellas almost make you feel like you're on a tropical island.
Across the street on the east side of Talbot Street is this sushi bar and grill. The palm trees and thatch umbrellas almost make you feel like you're on a tropical island.
Continuing north and looking back across the street we see some more businesses, including another ice cream place.  At this point the businesses and foot traffic becomes less dense as we leave the heart of downtown St. Michaels.
Continuing north and looking back across the street we see some more businesses, including another ice cream place. At this point the businesses and foot traffic becomes less dense as we leave the heart of downtown St. Michaels.
We look back across the street again where we find a small park.  Not visible in the picture is a historical marker explaining the history of Frederick Douglass in St. Michaels.  On the right, that small booth is an Information Center and behind that is a public parking lot.
We look back across the street again where we find a small park. Not visible in the picture is a historical marker explaining the history of Frederick Douglass in St. Michaels. On the right, that small booth is an Information Center and behind that is a public parking lot.
Across the street are some more colorfully painted structures that are now shops along Talbot Street.
Across the street are some more colorfully painted structures that are now shops along Talbot Street.
And across from that is a cafe, a gourmet store and a gift shop.
And across from that is a cafe, a gourmet store and a gift shop.
Continuing north, we find another gift shop, this time for pets.
Continuing north, we find another gift shop, this time for pets.
On the left is a gourmet restuarant and on the right is The Parsonage Inn, a Bed & Breakfast.  The house was built in 1870 but the tower was added in 1894.  It is the only example of a Queen Anne style building in St. Michaels.
On the left is a gourmet restuarant and on the right is The Parsonage Inn, a Bed & Breakfast. The house was built in 1870 but the tower was added in 1894. It is the only example of a Queen Anne style building in St. Michaels.
And just across the street is the Chesapeake Bay Maritime Museum.  It's not hard to miss.  You'll see the original Knapps Narrows drawbridge relocated right in the front driveway.
And just across the street is the Chesapeake Bay Maritime Museum. It's not hard to miss. You'll see the original Knapps Narrows drawbridge relocated right in the front driveway.
This takes us out of the St. Michaels Historic District.  You can continue driving east on Maryland Route 33.  It's a Maryland scenic route.  In 15 miles you will hit scenic Tilghman Island.
This takes us out of the St. Michaels Historic District. You can continue driving east on Maryland Route 33. It's a Maryland scenic route. In 15 miles you will hit scenic Tilghman Island.

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St. Michaels, Maryland

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