I grew up taking 2-3 trips a year to the Annapolis area because we have extended family down there. On average the drive is 5-6 hours and includes a jaunt over the GW Bridge and a trip through the big underground tunnel in Baltimore. We drove down to Annapolis over Labor Day Weekend for a friend’s wedding and although we got very little sleep and drank more than was standard we had a blast. Reviews/recommendations below!
Hotel: DoubleTree by Hilton Hotel Annapolis – about 3 miles outside of downtown
**Pros – Free shuttle to and from downtown until 11pm, free cookies, comfy mattresses, bar and restaurant in hotel, outdoor pool, and fitness center.
**Cons – Walls were super thin. If someone was talking in the hallway it sounded like they were standing in our room. Also, I HATED the pillows. But, hubby loved them so I guess that’s just preferential.
Eats/Drinks: All in Annapolis
Mission BBQ – This is a chain that we’d never been to before and they don’t have them in CT. We were obsessed and actually ate here once for dinner and once for lunch during our visit. We each got the pulled pork sandwich and mac n’cheese…both times….so good.
Pennsylvania Dutch Farmer’s Market – This is a farmer’s market style store run by Amish folks and is only open Thursday-Saturday. They have THE BEST doughnuts, pretzels, and cinnamon buns (all handmade on site) and have a heavenly produce section, meat department, and deli. The restaurant within the market is also amazing. It gets busy, but is worth the chaos.
Dry 85 – We were super excited to try this place for lunch, but both of our sandwiches came out on stale buns. Ambiance was great though. Dark wood, industrial style. We went back the next night for drinks and the sidecar was on point.
Red Red Wine – Food was reasonably priced, kind of light fare, but not the most flavorful. Again, ambiance was fun, wine bar vibes. I got a flight of pinot noir and was pretty pleased.
Today’s Pizza – We ordered a pizza at 1am, as previously mentioned there was excess drinking and little sleeping. It was hot and cheesy which was pretty much our only requirement for the night. Obviously doesn’t compare to our normal New Haven pizza standard.
Ports of Call – This is the restaurant in the DoubteTree Hotel and we had breakfast here before we checked out. The fruit and yogurt parfait was pretty good and the omelettes looked huge. They also have a breakfast buffet in the mornings. Pretty much your standard hotel restaurant.
It’s fun to be down in that area, do some shopping, and sit by the water. Overall it was a very relaxing, but busy weekend. Share your Labor Day Weekend getaway in the comments!