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24 Hours to Create Your Own Version of Wedding Crashers in St. Michaels

Updated: Nov 9, 2020

One and a half hours from Baltimore is a beautiful little town of St. Michaels. Most people may know it from the movie “Wedding Crashers.” It is the perfect place for one or two days. This was our third time visiting since October 2019, and every trip has been wonderful. This time we brought my parents to celebrate my father’s birthday. Here was our itinerary:

11:30 am – Arrive in St. Michaels and park in the free town parking lot.

12:00 pm to 1:30 pm – Enjoy brunch/lunch at Awful Arthur’s. We ordered: the Clam Chowder, the Lobster Bisque, two dozen oysters, two lobster rolls with fries, a Reuben sandwich with fries, and a lobster Reuben with fries. Delicious. Don’t forget to partake in some brunch drinks. The Rosé Spritzer and the spicy Bloody Mary hit the spot.

1:30-2:30 pm – Walk the few blocks to the Classic Motor Museum to check out beautiful cars and learn the history from an expert tour guide.

2:30-2:45 pm – Walk around and enjoy the waterfront area (take a picture!).

2:45-3:45 pm – Head back to the main street and do some shopping or grab ice cream at Justine’s. A shop we love is called “Take Me Home.” (For the women -- their lotions smell amazing). The shop owner is also super friendly.

Ice Cream at Justine's

3:45-4:00 pm – Take a water taxi or walk to the Inn at Perry Cabin (where the main reception scene from Wedding Crashers was filmed).

4:00-6:00 pm – Have some drinks and snacks at the pub inside the Inn or take your drinks outside and take in the peaceful view of the water. Pro tip: the Inn’s new tradition is to have a champagne toast at 5 pm every night.

6:00-7:30 pm – Walk back to town and head to a waterfront restaurant. We chose Foxy’s. Here is what we ordered: the ahi tuna, gnocchi mac and cheese, the crab pretzel, the crab cake sandwich, the burrito, and the tuna sandwich. The place is lively with great service and even better views.

7:30 pm – Time to head home.

From our previous trips to St. Michaels, here are some of the other activities we recommend:

Places to stay if you decide to stay the night:

  • The Inn at Perry Cabin – We hear it is wonderful to stay at the Inn. We plan on staying there sometime soon.

  • The Parsonage Inn – We stayed at this bed & breakfast on our last trip and had a great experience. The breakfast was delicious, and they even have bikes to rent.

  • St. Michaels Inn – On our first trip to St. Michaels we stayed at this Inn, and the only downside was that you still had to drive into town. Otherwise, we liked it. Very clean and comfortable.

Sunset by the Waterfront

Most importantly, don’t forget to see the world, and eat the food.


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