Travel Itinerary: How to Spend Your First Weekend in Ocean City

Check In For Your Stay

First thing’s first: Check into your hotel! No matter where you stay in town, you’ll be close to an array of must-visit spots. If you’re not sure which hotel is for you, explore our recommendations here! You can filter by location, amenities, and more to make choosing as easy as possible. 

Afternoon

It's time to grab an early dinner. As this is your first time ever dining in OC, the pressure is on! But, we have a few great recommendations. If you’re staying Downtown, kick off your vacation with dinner and drinks at Fish Tales. On the bay at 15th Street, Fish Tales is great for both ambiance and great food. Midtown? Go for Fager’s Island! This is a must-visit spot at some point during your stay, whether it’s for the food or nightlife. Finally, if you’re Uptown, grab some barbeque at Bull on the Beach on 94 Street!

Evening

Next up? Explore the boardwalk! You can’t visit OC without taking a stroll somewhere along the 3 mile stretch. If you visit the south end near the Inlet, you’re in for a world of excitement! Here, you’ll find Trimper Rides and Jolly Roger at the Pier. Go for a spin on the iconic carousel or feel the wind in your hair on one of the coasters! Enjoy some skee ball at Sportland Arcade or Fun City Arcade, and then grab a snack at Thrasher’s, Dumser's Dairyland, Fisher’s Popcorn, or The Dough Roller.

Nighttime

Spend your first night in town enjoying some classic Ocean City nightlife. We recommend kicking things off downtown, starting with The Bearded Clam. Here you’ll find a classic OC bar vibe. Follow that with a trip to the Crawl Street Tavern, and end your night on the water at The Angler and then M.R. Ducks. Here, you must chug a duck—it’s tradition!  All four spots are located downtown and within close proximity of one another, making it easy to hit each location.

Morning

Start your Saturday morning with a delicious breakfast. You have a lot of options, but we recommend trying out Bayside Skillet on 77th Street. This charming spot is an Ocean City classic that has been serving up incredible crepes and omelettes since 1977.

Midday

Finally, it’s time to hit the beach! Any part of town is perfect for a relaxing beach day. You can head Downtown to be close to the boardwalk, or find your spot in the sand somewhere Midtown or Uptown! Here’s everything you need to know about OC’s districts.

Afternoon

After a day spent soaking in the sunshine, grab a nourishing lunch from Anthony’s or Surfin’ Betty’s. Anthony’s is the spot for delicious and hearty subs and sandwiches. At Surfin’ Betty’s, you can find mouth watering burgers, chicken sandwiches, and hotdogs. And don’t forget a shake!

After lunch, it’s time for some excitement. How about an afternoon on the water? Enjoy a thrilling ocean ride with the Sea Rocket, or relax on a sail with Sail Alyosha.

Evening

You can’t leave OC without eating some Maryland crabs! Hooper’s Crab House is a great spot to indulge. If the evening calls for some fine dining, visit The Hobbit or Harrison’s Harbor Watch. The Hobbit offers gorgeous views of the bay, so it’s great to visit during the sunset! Harrison’s Harbor Watch is an Ocean City staple that boasts over 100 years of family tradition.

Nighttime

Round out the day with a night out at two iconic Ocean City nightlife spots: Seacrets and Fager’s Island! At Seacrets, you can dance the night away with live music in the nite club, or spend time by one of the other stages throughout the venue. Fager’s Island is another great spot to spend the evening with multiple bars, live music, and gorgeous decks overlooking the bay.

Morning

Kick off your last day in town with an incredible brunch from Barn 34. They offer everything from benedicts and crabby eggs to classics like omelettes and french toast. You can also enjoy acai bowls, avo toast, or Nutella waffles!

Midday

After brunch, spend your last few hours in town doing some souvenir shopping at some of Ocean City’s classic spots. At K-Coast and Malibu’s, you can find surf apparel to commemorate your trip. Both shops have been around for decades and offer a great sense of OC nostalgia! The Kite Loft is also a must-visit spot. Their stores are colorful wonderlands of every kite style you can imagine! 

Enjoy the full itinerary list below:

Friday

• Get into town and check into your hotel.

• Grab a bite at Fish Tales, Fager’s Island, or Bull on the Beach.

• Explore the boardwalk! Ride the rides at Trimper Rides and Jolly Roger, visit Sportland Arcade and Fun City Arcades, and grab snacks at Thrasher’s, Dumser’s Dairyland, Fisher’s Popcorn, or The Dough Roller.

• Hit downtown for a night out at The Bearded Clam, Crawl Street Tavern, The Angler, and M.R. Ducks.

Saturday

• Grab breakfast at Bayside Skillet.

• Hit the beach anywhere in town.

• Enjoy lunch from Anthony’s or Surfin’ Betty’s.

• Spend some time on the water with the Sea Rocket or Sail Alyosha.

• Enjoy crabs at Hooper’s Crab House or fine dining at The Hobbit or Harrison’s Harbor Watch.

• Enjoy another night out at Seacrets and Fager’s Island.

Sunday

• Have a nice brunch at Barn 34.

• Do some shopping around town at K-Coast, Malibus, and the Kite Loft.

• Head home & start planning your next trip to OC!