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Best Ocean City MD Restaurants for Teachers to Unwind
School is out, the lesson plans can wait and it’s time to unwind! Here are some of our favorite Ocean City, MD restaurants for teachers looking for drinks, dinner, waterfront views and a fun night out with coworkers.
By Katie RuskeyOctober 5, 2026Updated October 11, 20265 min read

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Coming to Ocean City for the MSDE Convention next weekend? Once the sessions wrap up, the professional development is done and you’ve officially spent enough time talking about education for one day, it’s time to put the conference badge away and enjoy a little Ocean City. Here's a list of restaurants and bars where teachers are welcome to unwind.
Need a Drink and a Little Fresh Air?

The Wedge Bar
The Wedge Bar is a great casual option for teachers looking to unwind without making a whole production out of it. With indoor and outdoor seating, drinks, burgers and tacos, it’s an easy spot to meet up with a few coworkers after school. And the view of the Ocean City Inlet and Assateague Island is unmatched.
Angler
Angler is another easy choice for a teacher crew. It’s casual, comfortable and offers plenty of options for a group that may not all agree on what they want to eat.
Grab a drink during their two for one happy hour, split some food or keep it simple with one of Angler’s pizzas or slices. It’s the kind of place where you can show up in your “I just survived the school day” clothes and nobody is judging.
Need to Actually Relax?

Spain Wine Bar
For the teacher who would like to trade the classroom noise for a glass of wine and a conversation that doesn't involve the words “turn your paper over,” Spain Wine Bar is a great choice. With Spanish-style small plates and wine, it’s a nice option for a smaller group looking for an upscale night out.. This is the place for lingering over dinner, catching up with coworkers and letting the school day officially end.
Kalamata
Kalamata is another great option when teacher night needs to feel a little more like a night out. Share some Mediterranean-inspired dishes, order a cocktail and enjoy the lively atmosphere. And if you happen to go on a night when the belly dancer is performing (Saturdays), you’re definitely getting more entertainment than you would during your average Tuesday staff meeting. Kalamata is especially good for a group of friends or coworkers who want to turn an ordinary night out into an actual occasion.
Need a View With That?

Harrison's
There are few things better after a long week than sitting down to a good meal with a view. Harrison's is a great option for teachers who want to slow things down a little. Fresh seafood, hot meals, bar seating or a table and those beautiful waterfront views make it easy to settle in and stay awhile. Order the oyster stew, grab some fresh fish and let someone else do the cooking for a change.
Vista Rooftop
Sometimes the best way to unwind is to go somewhere that feels like you're actually on vacation. Vista Rooftop offers the views, drinks and atmosphere for a teacher night that feels a little more special. Grab your coworkers, head up to the rooftop and enjoy the scenery while you decompress.
Need to Let Loose a Little?

Shenanigan's
If your teacher crew is looking for something livelier, Shenanigan's brings plenty of energy. This is less “quiet dinner and home by 8” and more “we survived another week, let's have some fun.” Grab food, drinks and enjoy the lively Ocean City atmosphere with your coworkers. And then take on the boardwalk when you're done!
Crawl Street Tavern
Crawl Street is another good choice for a group that wants dinner and drinks without taking themselves too seriously. It's casual, social and easy to turn into the beginning of a bigger night out if the group decides they're not quite ready to go home yet. Crawl Street typically has live music, too!
Guido's
A plate of chorizo nachos and a top-shelf margarita sounds like a pretty good way to end a school week. Guido's is a fun option for teachers looking for a casual dinner with plenty of personality. Grab a table overlooking the boardwalk, order some food and let the conversation move far, far away from lesson plans. Guido's also has a great neon selfie sign- "Feed me tacos!" which will help you remember the great time you had.
Taking the Whole Team?

Captain's Table
If this is less “a few coworkers grabbing a drink” and more “the entire team needs to get together,” Captain's Table is worth adding to the list. It's a good option when you want to sit down for dinner, catch up with coworkers and actually have time to talk. If you go on Friday or Saturdays, they have live piano music which adds to the relaxing ambiance.
Pickles Pub
For something more casual and social, Pickles Pub is another easy group option. It's the kind of place where a group can grab food and drinks, relax and enjoy a little friendly conversation after spending all day surrounded by elementary-school-level chaos. I highly recommend challenging a co-worker to a game of pool or a dance off during their live music!
And Sometimes You Just Need Coffee...And Donuts

Quickies
Not every outing has to involve dinner and drinks. Sometimes you need coffee. Or a donut. Or both. Quickies is a great option for the teacher who would rather start the morning with coworkers than end the day with them. Grab coffee and a cinnamon donuts, catch up before the conference or make it your reward for surviving the week. Because let's be honest: some weeks require a little extra sugar.
Teachers Deserve a Night Off
Teaching is a lot. It's rewarding, exhausting, hilarious, frustrating and occasionally all of those things before 9 a.m. So when Friday finally arrives, give yourself permission to close the laptop, leave the grading for Monday and go enjoy Ocean City.
Grab your coworkers. Pick a restaurant. Order something you didn't have to pack yourself. Stay for one more drink. Laugh about the ridiculous things that happened during the week.Because tomorrow can worry about tomorrow.Tonight, you’re off the clock.
About Katie Ruskey
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