A Dog-Friendly Annapolis Day Trip

Annapolis is one of the most popular day trips from DC, and for good reason. It’s beautiful location on the Chesapeake Bay, a reputable dining scene and a boatload of history provide something for everyone. A few weeks back, we decided to take the dog along and see what pet-friendly adventure we could get up to in Maryland’s state capital.

Tips for Your Dog-Friendly Annapolis Day Trip

Have Brunch at Iron Rooster

Dog-friendly restaurants are not hard to come by in Annapolis, but you’d be hard pressed to find a better brunch with your pup than at Iron Rooster. Waits are long for this popular restaurant, but having Ashton with us actually worked to our advantage. A table had just opened up on the small patio when we arrived and we were seated right away. Service was excellent and catered to our canine companion by bringing him a bowl of cold water.
We humans enjoyed some adult beverages, delicious bacon bloody Marys with killer garnishes – pretty much a meal in and of itself.
The food was excellent as well. I ordered a watermelon and arugula salad, but kept stealing bites of Tom’s smoked brisket benny with a jalapeno cornbread waffle, fresh tomato salsa and caramelized onion.
A long day of exploring calls for plenty of fuel, so of course we had to try a house made tres leches pop tart. While there was perhaps a bit too much crust and not enough filling for my liking, you can’t go wrong with all that gooey caramel.

Take a Stroll Down Ego Alley

Ego Alley is the place to see and be seen in Annapolis.
Since we don’t have a boat to show off, our dog was the next best thing.

Go for a Boat Ride on the Bay

Looking at boats is nice, but in the summer heat it’s far preferable to be on one. Luckily, Watermark Cruises on the Bay offers dog-friendly Annapolis cruises at reasonable prices.
We chose to embark on the Chesapeake Bay Bridges cruise, which departs weekend days at 2:30 and Fridays and holidays, too, during the peak season.
This cruise has a lot going for it. The boat is spacious and air-conditioned and the staff are incredibly helpful and friendly. It did feel a bit crowded at times, but the relaxation that comes with being on the water was definitely worth it.
The cruise features a narrated history of the area, which was hard to hear at times but quite interesting. We ambled along for a while taking in the sites before coming to the main event – spectacular views of the Chesapeake Bay Bridge.
If you live in the area, you’ve driven over the massive bridge many times. If you’re like me, you’ve white knuckled it the entire way every time. I have a major, irrational fear of bridges and just the thought of driving over this thing upsets my stomach.
However, riding under it in a boat with a Corona in hand is the opposite of scary. I love getting new perspectives of familiar sites, and this really delivered in that aspect.
Note: In addition to being dog-friendly, this particular cruise was also very family friendly. A full bar is provided, but if you’re looking to get wild and crazy you may want to try another boat.

Get Lost in the Endless Scenery

Annapolis is beautiful. After our cruise, we simply wandered around taking in all the breathtaking views.
A storm was about to roll in, so we were treated to pastel skies in addition to the calm waters and natural beauty of the city.

See the U.S. Naval Academy

It was actually too hot for us to do this during our trip, but if you’re in Annapolis on a nice day a trip to the Naval Academy is a must. Your dog will enjoy the exercise as much as you enjoy the sites.

Enjoy a Casual Dinner at Davis Pub

Avoid the ample touristy restaurants along Ego Alley and head to Davis Pub, a local favorite in the charming Eastport neighborhood.
There’s so much to love about this unpretentious little bar. Prices are great, food is delicious and they even have a special menu for pups.
We weren’t too hungry, so we shared a delicious crab cake platter and house salad, all very tasty.
I’m sure there are some non-dog people out there who probably think we’re insane for taking Ashton with us to so many places, but it’s what works for us. Besides, he’s incredibly well-behaved and about as cute as they come.
But I’ll be the first to admit that, yes, I’m a crazy dog lady and I have no intention of changing that anytime soon.
For more tips about traveling with your pet, check out this post.
What’s your favorite day trip from your city? Do you ever take your pet along?
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