St. Michaels, MD – The Complete Guide To Visiting

St. Michaels is a very small, charming town located on the Eastern shore of MD. It is located about an hour away from Annapolis. It’s two hours from Washington, DC.

History of St. Michaels

The town of St. Michaels is often referred to as the town that fooled the British. There is a lot of history around this area. As one story goes: In the war of 1812 the citizens of St. Michaels were forewarned that the British ships were attacking at nightfall. They cleverly moved all of their lanterns from their front porches to the trees beyond the town. Thus in turn when the British ships fired their cannonball they thought they destroyed the town, but instead missed all of the houses except for one. Hitting the trees in the distance instead…and with that, the town was saved!

St. Michaels continues to exude its same pride & colonial charm today. The locals love their little town and upon arriving you will too. There are a plethora of Restaurants, Bars, & Shops to visit!

If you can, head straight for the Information Center. It’s located right on the corner, across from Justine’s. It’s adjacent to the public parking lot as well as the restrooms. There you will find a brochure for just about every restaurant, shop, and recreational activity St. Michaels has to offer!

Let’s talk food:

St. Michaels Crab & Steak House

It’s all about the great view. It’s located right on the water. This local staple was apparently an oyster shed back in the 1800’s. Its right next to the marina. Sit outside! You can enjoy some MD favorites with a nice breeze coming in off of the harbour.


  • Tropical Crush (made with house-infused pineapple vodka!)
  • Dark and Stormy
  • Bloody Mary (made with house-infused vegetable vodka!)
  • Rockfish Bites
  • Seafood Skins
  • Softshell Crabs
Ava’s Pizzeria& Wine Bar

Fresh made Italian style food (also feat. fresh local seafood) that’s received numerous awards over the years. You can count on a delicious and satisfying meal. They even make their own pasta!

Ava’s is also pet friendly 😉 Leashed dogs are welcome on the patio and they even offer a pet menu. Besides offering a family friendly menu, it’s also a great place to stop for some appetizers and wine!

Shrimp Fra Diavolo at Ava’s


  • Wine (with an extremely extensive wine list – there’s definitely something for everyone!)
  • Local Beer (There are lots of local beers available.)
  • St. Michaels Mule
  • Maple Bourbon Old Fashioned
  • Damian’s Wasabi Oysters
  • Ma’s Meatball Sliders
  • Ava’s Seared Short Rib
  • Chef’s Favorite Specialty Pizza (with crispy prosciutto and a balsamic reduction)

Blackthorn Irish Pub

A lively little pub in the middle of town. During the day there is a little something for everyone, while at night they have plenty of events & music going on.


  • Fighting Irish Mojito
  • Reuben Egg Rolls
  • Buffalo Shrimp
  • Fried Pickles
  • Fish & Chips


Limoncello is an Italian restaurant serving up authentic and approachable Italian dishes for lunch and dinner!


  • Burrata & Pomodori
  • Fettuccine Bolognese (This is my personal favorite!)
  • Paccheri alla Amatriciana

The Crab Claw

The Crab Claw has a great view of the water. It’s the perfect atmosphere to grab a beer and some crabs. It’s located right next to the Maritime Museum.


Justine’s is a local Ice Cream Parlor that you can’t miss on your next visit! They were named one of the top ten ice cream shops in the United States! They serve up high quality ice cream with innovative as well as classic flavors such as Butter Pecan, Cookie Dough, and Rum Raisin. They also have a wall of shakes with over 50 different flavors over the years, like the Mudslide Shake, Key Lime Shake, or the Chocolate Covered Cherry Shake!


St. Michaels even has it’s own brewery, winery, & distillery! Another great way to pass the time.

Eastern Shore Brewing

The official Brewery of St. Michaels. They’ve been brewing beer for ten years! You can enjoy flights, pints, or even purchase growlers to go! Eastern Shore Brewing Beers are also carried inside many of the local restaurants/stores.


  • St. Michaels Amber Ale
  • Back Creek Blonde
  • Blue Heron Coffee Porter
  • Pucker Up

St. Michaels Winery

The local Winery. No need for reservations. There are daily wine tastings, as well as Wine by the bottle or glass available for purchase. Like the local beer, you can also find this local wine available in most of the restaurants and stores around town!


  • Chocolate Zin
  • Gollywobbler Peach
  • Oakey Dokey Chardonnay

Lyon Distilling Company

They’ve been creating ultra small batches of high quality liquor since 2013. The Distillery’s founder Jaime Windon spent years as a bartender and traveled all over the world developing and refining her knowledge and tastes for perfectly balanced cocktails. You can visit the Distillery and taste it for yourself as well as enjoy a behind the scenes tour! They specialize in Rum, but are proud to offer other spirits as well. Not only can you enjoy and buy these liquors from the Distillery you can also purchase them in various stores all over Maryland.

Blue Heron Coffee

A specialty small batch coffee roaster. This coffee shop is in a convenient location right in town, next to the Shore Paddle Store.

Rise Up Coffee

This coffee stand is right at the beginning of town near the local grocery store and the gas stations. You can drive thru or walk up. If youre staying near the Harbor it’s a little bit of a longer walk, BUT totally worth it!! Rise Up is one of my absolute favorites. They are locally owned with other MD locations including one in Easton where they roast a lot of their coffees! They offer seasonal flavors as well like my favorite Mocha Coconut!


St. Michaels also has lots of amazing events constantly going on in town.


The Winefest is a weekend full of fun. Usually in late April,  but its best to double check the website to verify the dates and purchase your tickets ahead of time. You can explore St. Michaels and visit multiple wine tasting venues throughout the town. It features more than 300 wines from around the world. They also give back to various charities that actively help the community.


The BrewFest is usually held in June. You can sample hundreds of beers with local origins as well as plenty of worldwide brews! Similar to the winefest you purchase tickets and there are a couple of tasting locations throughout the town.

Here are a few other festivals throughout the year, you may be interested in:

Daffodil Festival
Sea Glass & Coastal Arts Festival
Christmas in St. Michaels
Chocolate Fest

Shop Til You Drop

The shopping is abundant. There are numerous stores offering everything from clothing and fine jewelry to confections, home decor, souvenirs, and local so much more!

There are also numerous places to rent bicycles, paddle boards, and canoes.

Shore Pedal & Paddle – They are located in the heart of town. They offer rental of all of the above as well as paddle boarding lessons!

Maritime Museum & The Patriot

The Maritime Museum is also a great place to spend some time. After you stroll through the museum be sure to take a cruise on the Patriot. It’s a great way to see St. Michaels by water.

Places To Stay

Inn at Perry Cabin

The Inn at Perry Cabin is a top notch Inn, Spa, and Golf Resort located right in St. Michaels.

The rooms are charming, elegant, and comfortable.

There is SO MUCH TO DO!

Below I’ve listed some of the many activities available, to give you an idea of all of the amazing amenities The Inn at Perry Cabin offers.

  • You can experience Sailing for yourself by going out on a group sail or arranging a private tour complete with lunch and sunset cocktails!
  • Or enjoy the day with a golf course designed by the legendary Pete Dye.
  • There are also tennis courts and bicycles available for everyone. Which is perfect because exploring the town by bike is a wonderful option!
  • Plus, you can even grab a paddle board or kayak and explore the beautiful Miles River.
  • Maybe a relaxing spa treatment is more your thing. They have a luxurious spa that offers therapeutic and plant-based treatments made from herbs grown in their own garden. Everything from body massages to nail treatments.

There is an onsite restaurant as well as a pool bar. Private dining is also available. They source fresh, seasonal ingredients from the farmers and fisherman of the eastern shore!

The Old Brick Inn

Rustic charm in the heart of St. Michaels, MD. They offer 20 rooms in the main inn and 2 additional guest houses. As well as a restaurant.

Victoriana Inn

Located in St. Michaels right on the harbor within walking distance to the Maritime Museum and all of the restaurants and shops! The rooms are charming and they offer a full hot breakfast for all guests to get the day started off right!

St. Michaels Harbour Inn Marina and Spa

St. Michaels Harbour Inn Marina and Spa is owned by a local family. They strive to make guests feel at home. The Inn is located right on the water. They have an onsite restaurant Harbour Lights. As well as a pool and a Spa perfect if you’re in need of a relaxing massage. They even offer a marina, if you’re arriving via boat! They have various Suites available to meet all of your vacation needs.

Whether you’re visiting St. Michaels, MD for the day or a long weekend you’ll find plenty to do and lots to see in this charming waterside town!


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  • Reply
    July 2, 2019 at 3:14 am

    Glad to learn that it is pet friendly place and I love the Shrimp Fra Diavolo at Ava’s, the shrimps look super delicious and I can’t wait to take a big bite.

  • Reply
    katie davies
    July 2, 2019 at 4:06 am

    oh what a great story i have never heard that before. this looks like such a quaint and pretty town I’d love to visit one day

  • Reply
    July 2, 2019 at 7:17 am

    That looks like such a cute little town. I LOVE visiting places like this. It makes me feel like I’m traveling back in time.

  • Reply
    Melissa Dixon
    July 2, 2019 at 8:18 am

    That looks like a beautiful place to visit. I would love to head back to the East, I grew up out there and there is just so many things to show to my family that they could not get out here.

  • Reply
    Romy Schorr
    July 2, 2019 at 8:56 am

    What a fun place to visit. Your guide is awesome for anyone that wants to visit and know what or where to go.

  • Reply
    Lauryn Hock
    July 2, 2019 at 12:22 pm

    What a cute little town! The shrimp dish looks heavenly.

  • Reply
    July 2, 2019 at 1:30 pm

    Such a great place to visit over the summer. I’d love to visit…looks like my kind of town!

  • Reply
    July 2, 2019 at 1:53 pm

    What a great place to visit! Perfect for the summer time 🙂

  • Reply
    July 2, 2019 at 3:42 pm

    I can only imagine the beautiful stories local must have and the feeling of peace you get while strolling down the harbor.

  • Reply
    July 2, 2019 at 4:53 pm

    Looks like a very cozy and inviting place to visit. I’d love to visit in the summertime.

  • Reply
    Fiona Cambouropoulos
    July 2, 2019 at 6:21 pm

    Looks a lovely place to visit. Not too touristy and full of charm with so many different shops, bars and places to eat. A bonus being on the water.

  • Reply
    July 2, 2019 at 7:11 pm

    This town isn’t that far at all from me – just a roadtrip away! I’ll have to plan a trip with my husband sometime. It has such a cute, small town feeling that looks really appealing. And anywhere with good food is up my alley!

  • Reply
    Mama Maggie's Kitchen
    July 2, 2019 at 7:37 pm

    Wow! This place sounds really awesome. Can’t wait to visit!

  • Reply
    Lisa Rios
    July 2, 2019 at 8:54 pm

    I love the history behind this town! Landmarks are always so fascinating to me!

  • Reply
    July 2, 2019 at 10:26 pm

    Ah this is my kind of place right here. No doubt we’d hit up that steak house while there too!

  • Reply
    July 3, 2019 at 1:16 am

    Sounds like such a great place to visit!! Definitely want to make a trip out sometime, that Crab Claw sounds amazing!

    cute & little

  • Reply
    Sondra Barker
    July 3, 2019 at 4:23 am

    This looks like a great summer trip and that food is making my mouth water! Thanks for sharing -Sondra Barker

  • Reply
    Ginger Sorensen
    July 3, 2019 at 6:36 am

    My husband and I want to start traveling more and these little gems are exactly what I want to start exploring.
    Thanks for sharing about this place. Adding it to my list of spots to travel to!

  • Reply
    alexandra cook
    July 3, 2019 at 10:29 am

    what a perfect view! I will definitely look something more abt this place and try to visit,

  • Reply
    Yeah Lifestyle
    July 3, 2019 at 12:04 pm

    Such a lovely place to visit even as a day trip, St Michaels has some nice views and great food too which I would love to try

  • Reply
    July 3, 2019 at 12:37 pm

    This looks like such a gorgeous place to visit. I love how quiet it feels but with so much to do!

  • Reply
    July 3, 2019 at 12:59 pm

    I want some Shrimp Fra Diavolo for my lunch today. It looks so good.

  • Reply
    July 4, 2019 at 12:19 am

    Wow what a detailed list of the things to do! Saving this for my travels!

  • Reply
    Jackline A
    July 4, 2019 at 11:03 am

    Great travel guide and information. Never heard of St. Michael’s but it looks beautiful.

  • Reply
    July 5, 2019 at 5:26 am

    What a gorgeous place and such an amazing history didn’t know it foiled our troops, pretty impressive

  • Reply
    July 5, 2019 at 11:47 am

    What a great guide you made wow! Thank you so much! Looks like a blast! Saving this for my travels!


  • Reply
    Kalyan Panja
    July 7, 2019 at 10:52 am

    I love visiting off the beaten track destinations and this city sounds absolutely amazing with all its history, architecture and food too.

  • Reply
    Denise Kokinis
    July 8, 2019 at 11:51 am

    I had no idea that this town had a fun colonial history to it! What a cute and quaint place, especially since it feels like small town America! Loving the food options too!

    Denise | Fashion Love Letters

  • Reply
    Megan Elliott
    July 8, 2019 at 3:48 pm

    This town is just TOO cute!! It looks like the perfect summertime destination. I absolutely love the history behind it too! So fun.

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