8 Minute Speed Dating Near Ocean Pines Md

Ocean City, Maryland (“O.C.” for short) is our state’s largest resort town located on the Eastern Shore in Worcester County. While it boasts more than three million visitors per year during the peak season (Memorial Day to Labor Day), less than 10,000 residents live in the town year-round.

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The majority of Ocean City is part of the Fenwick Island Barrier Spit, a very thin barrier island that extends from southern Delaware into Maryland and contains a number of beach towns including Bethany Beach, Fenwick Island, and Ocean City.

While O.C. is known for its family-friendliness, we also like it as a getaway for just the two of us when we’re looking for sunshine, ocean views, and peace and quiet. Ocean City offers well-maintained beaches, many good restaurants, a three-mile boardwalk, a large inlet bay, dozens of amusements, and nearby Assateague Island National Seashore, famous for its wild horses.

Ocean City holds a special place in our family’s heart and we’re excited to share it with you and your family via this guide. We’ve designed the guide so you can read straight through or pick a topic that interests you most. Dating agency near johnston ri island.

O.C. Guide Contents

  • Our Ocean City Restaurant Picks
  • Attractions We Like
  • Special Events & Holidays

Why We Love Ocean City

Kim and I both grew up in the greater Baltimore area about 150 miles from Ocean City. Both of our families vacationed on the Delaware and Maryland beaches, hers with their 7-person camping trailer and ours by renting apartments downtown or using a condo my grandfather bought when I was 8 years old. As teenagers we attended retreats in Ocean City with our churches in the off-season.

Now that we’re the parents, we want to hand down our families’ vacation traditions to our kids.

Every place we review and recommend in this guide our family has tried at least once. Some places we’ve been dozens of times. Others, like Go Karts at Baja Amusements, are once-a-year earned rewards for school performance due to their higher price tag.

Our Home Away from Home on 94th Street

We like Ocean City so much that two years ago we purchased a three bedroom oceanfront condo in The Flying Cloud, a mid-rise building just north of 94th street on the island. We chose The Flying Cloud for its location in the northern part of the town, which tends to be slightly less crowded in the on-season while still being close to everything O.C. has to offer.

We use the condo as our family’s beach home several times a year and rent it out the rest of the time. If you’re interested in traveling to O.C. and renting from us, you can view more photos and details of the place or check our availability on VRBO. We typically book up for peak season by mid-February.

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Here’s Kim pointing to our unit the day we came down for inspection about a month before we closed. Even after owning it for two years, we still love every minute we get to spend here.

How to Choose a Place to Stay in O.C.

Step 1: Rent from us. Step 2: You’re done.

Just kidding :-).

There are literally thousands of options for places to stay in Ocean City, from hotels and motels to individually-owned condos and town homes. Here’s the things we think are most important to consider if you’re new to Ocean City and trying to understand the different lodging choices.

North vs. South: Like all barrier islands, Ocean City is long and narrow. The island stretches seven miles from where the Route 50 bridge enters at the southern tip to the Delaware line on the north end. Coastal Highway runs the length of the island, dividing the island into “bay side” and “ocean side” areas. Cross streets are numbered 1st to 146th from south to north. Route 90 enters the island at 62nd Street at roughly the mid-point of the city. Assawoman Bay lies to the west and the Atlantic Ocean to the right. Most of the island is no more than a quarter mile wide.

In general, the south end of the island (cross streets 1st to 33rd) tends to be louder and more crowded, especially in the on-season. This area (called “downtown” by the locals) has the boardwalk, the inlet amusements, the Jolly Roger Amusement Park, and hundreds of hotels and condos for rent. During peak season traffic is very heavy in this area, especially on Saturday and Sunday changeover days. This area is also most prone to flooding in severe weather events because it is lower lying than the northern part of the city. On the up-side you will never be bored; there is always something happening!

Mid-town offers restaurants, shopping, the Convention Center, and the hotspot Seacrets.

The north end of the island tends to be slightly quieter and less busy, though in recent years the north end has filled in considerably. There is hardly any buildable land left on the island. North Ocean City is home to the town’s high rises and more feature-rich resorts, like Golden Sands, The Capri, and The Plaza. Our mid-rise building is located between two high rises, 9400 to the south, and O.C.’s most iconic high rise, The Pyramid, to the north.

Ocean vs. Bay & Proximity to the Beach: Whether you choose north or south for your stay, we think the most important decision you can make is whether you stay bay side or ocean side and whether your unit has a waterfront view. The more expensive places in Ocean City have a direct oceanfront view. The further you get away from the ocean, the cheaper units tend to be, with the exception of direct bay front locations which can also be pricey.

If you plan on going to the beach during your stay, we definitely recommend staying as close to the ocean as you can afford so you don’t have to cross Coastal Highway carrying umbrellas, beach chairs, and coolers. If you can afford a direct oceanfront unit, it is really nice to be able to walk right out of your building onto the sand and sit on the balcony watching the waves at night. If you need to use the bathroom while the family’s on the beach, it’s also a much easier trip back to the place.

‘Ocean Front’ vs. ‘Ocean View’: Many places advertise ‘ocean views’. Sometimes these views are through a narrow gap between two buildings that are closer to the beach than the one being advertised. Ocean view condos should rent for less money than direct ocean front units. Some offer great views, others not so much.

This is the view from our oceanfront unit at The Flying Cloud. Many direct oceanfront properties offer similar views.

Check the Floor: If you’re staying direct oceanfront, you’ll want to make sure you’re staying on a floor that has a view over Ocean City’s dunes. Some older buildings have first floors that are so low their view is completely obstructed by the dune. In very low buildings even second floor’s views can be partially obstructed. Newer buildings tend to be built with tall garages under the first floor and are fine. Before you rent, ask whether you’ll be able to see the ocean clearly while sitting on the balcony.

It’s also important to know that most low-rise buildings in Ocean City don’t have elevators. If you have trouble climbing steps, make sure your unit is either on ground level or the building has an elevator.

Balcony Type and Location: There are at least two oceanfront buildings that do not offer traditional balconies with railings. If you’re idea of a good view is sitting and watching the ocean from your unit, make sure your balcony has a traditional see-through glass or baluster-style railing. It stinks to have rented an oceanfront place only to realize you didn’t get the view you paid for.

Additionally, some of the northern resorts including The Plaza and Golden Sands have pools and bars that sit on ocean side decks in front of the actual condo units. While these are really convenient during the day, you may be listening to a lot of crowd noise on your balcony at night. When we purchased our unit, top on our list was an unobstructed view of the beach.

Pools, Hot Tubs, and Exercise Rooms: If a pool is important to you, make sure to ask. Some buildings have indoor and outdoor pools, while others have neither. Some buildings have exercise rooms that are available for renters, others limit exercise equipment to owners.

Hotel vs. Independent Owner: As an independent owner in O.C., we think this is a no-brainer. Hotels certainly offer predictability and booking convenience, but individual units tend to have more character and are often better-located on the island. We use and recommend Airbnb and VRBO both as owners and travelers.

When to Book Your Stay

If you’re planning to go to O.C. during peak season (late June through early September) you should be booking your place no later than February. Most of the good units, and especially those that are favorably priced, are gone by the end of February. Our unit is typically booked solid for peak season by February 15 and we start getting reservations for summer weeks as early as 12 months in advance. During the off-season there is far more inventory than visitors and so your negotiating power goes up.

Peak season in Ocean City is Memorial Day to Labor Day. During the first three weeks of June, graduating high school seniors descend on the island in droves (it’s a Maryland tradition). While most of these seniors cause no trouble at all, a small minority of them give the whole group a bad rap. If you travel to Ocean City during these weeks, we recommend avoiding downtown for lodging. The downtown area has many lower priced units that attract the senior crowd. You’d be surprised how many they can pack into a one bedroom apartment :-).

Ocean City Eats – Our Favorite Places to Dine

We like just about everything Ocean City’s restaurant scene has to offer, from boardwalk grub to fancy eats.

Pricier Lunch and Dinner Spots

The Crab Bag, bay side 125th Street – We like this joint because it’s open until midnight on Friday and Saturday all year long. Since most of our Packing for Two trips start after work on Friday evening, we frequently hit The Crab Bag when we get into town around 9:00 pm. We really like their cream of crab soup, buffalo wings, and onion rings. We’ve ordered hard shell crabs a few times and they were good, though not different from what you get most places. Steaks and other seafood choices are also decent, and we’ve never had a meal we didn’t like. Crab Bag’s prices are on the higher end of retail, and they charge a “2% surcharge” on all checks for no obvious reason. (We think maybe they had to do this for market reason one season a while back and just never dropped it.) Because of the higher prices we tend to get sandwiches or appetizers and avoid the entrees. The one exception to this was when we took the whole family here to celebrate L’s adoption finalization in 2015. We got the call on the way to the beach and just had to pick a place to celebrate. That meal, including crabs, cost $300. Figure on $40 for two people who stick with light eats all the way up to $100 for a couple eating crabs and drinking adult beverages.

Hooked, bay side 80th Street – Hooked is on the nicer end of the dining scene in O.C. In other words, they’ve got tablecloths. Kim and I have only eaten at this place once and it was a good experience. I can’t remember what I ordered, but Kim ordered the Whole Fish. I don’t know exactly what we were expecting when she ordered that, but what we should have been expecting was literally a whole fish, eyes and all. Kim had to cover up his eyes because it was too sad to eat him while he could still look back at her! Prices at Hooked are on the higher end, but most will find it worth it for the nicer atmosphere. Expect to pay around $75 for two. We’d recommend considering this place if you’re celebrating an event.

Waterman’s, Route 50 west Ocean City – When we’re in the mood for all-you-can-eat crabs, this is where we go. A number of places in Ocean CIty offer all-you-can eat specials for prices ranging between $35 and $45. Waterman’s comes in on the lower end of the group at $37 and the special includes all-you-can-eat large and medium steamed crabs w/ Old Bay, steamed shrimp, fried chicken, hush puppies, and corn on the cob. We’ve gotten crabs at Crab Bag, Higgins, Phillips, and Waterman’s, and Waterman’s has consistently delivered the best price-for-taste ratio in our experience (though all of those will deliver a decent eating experience). Waterman’s has a large dining room but wait times can be over 90 minutes in the on-season, and they don’t accept call ahead seating. We recommend giving them a call before you head over to see how long you might have to wait.

The Bonfire Restaurant, bay side 70th Street – If you want to stuff yourself, this is your place. Kim and I don’t eat here when we’re traveling alone. We’ve gone twice with the kids and they love it. We like the food well enough, especially the snow crab legs, but it’s not remarkable for a meal alone. If you really like golden corral and are willing to pay 3x more to have seafood instead of sirloin, you might like the Bonfire. The biggest drawback here is that they don’t offer hard shell crabs as the restaurant isn’t setup to deal with the mess.

Horizons (in the Clarion Hotel), ocean side 101st Street – Kim and I ate here once for dinner and it was great. The Clarion offers one of the few sit down restaurants in Ocean City with a spectacular view of the ocean. Unfortunately we went to the restaurant after dark and while the food was good, it was too dark to see the ocean. This place offers a breakfast buffet and a seafood and prime rib buffet for dinner. When we went for dinner we ordered steaks and crab cakes off the menu and the food was delicious. The atmosphere is definitely dated; it looks like it was last updated in the early 90s. But with good food and an amazing ocean view, we still keep this on the recommended list. Prices here are higher. Expect to pay $80-$100 for two.

Less Expensive Lunch and Dinner Spots

Tequila Mockingbird Mexican Restaurant, bay side 129th Street – This is our go-to Mexican joint in O.C. They start you out with free chips and freshly made salsa that is some of the best we’ve ever had. (Minor drawback: they only give you one free serving; you pay for refills). Our go-to meal here is their steak fajitas. We typically split a single order and just ask for a few extra tortillas. We’ve also tried their burritos, enchiladas, tacos, and nachos and neither we nor our kids have ever had any complaints. The best part of Tequila Mockingbird is their prices. If you split an entree (they are typically big enough to split), you can get out without alcohol for $25, tip included. Throw in two margaritas (which we highly recommend if you’re traveling just the two of you) and you’re price rises to $40 or so.

Lombardi’s Italian Restaurant, bay side 94th Street – Located just across the street from our condo, we consider this to be the best pizza place on the island. Lombardi’s offers traditional NY style brick-oven pizza that tastes great. We typically go here with the kids, but if you’re looking for a moderately priced lunch or dinner, Lombardi’s is a great choice. They also offer a range of other Italian foods, most of which we haven’t tried.

Guido’s Burritos,bay side 33rd Street – Just like the name sounds, Guido’s is a Mexican joint closer to downtown O.C. We’ve eaten there once and had a fine experience, but have decided that we like Tequila Mockingbird better. If you’re staying on the south end of O.C., you might give Guido’s a try.

Breakfast and Brunch Joints

The General’s Kitchen, bay side 66th Street – We go to “GK” more than any other breakfast restaurant on the island. For years The General was located ocean side at 73rd Street. A few years back the owner of the property decided to toss GK to the curb in favor of starting their own restaurant in the space. (The new restaurant is called Coaches Kitchen, and we’ve never eaten there.) GK is now located on the first floor of The Skye Bar, and even though they haven’t had time to rework the decor in the space, they now have much more seating, which has reduced the wait. GK is famous for their chipped beef, though we aren’t really chipped people. We like their french toast, omelettes, eggs, and breakfast meats. While GK often has a line out front, it moves quick. Service has always been fast and friendly. Breakfast can run you as cheap as $20 or as much as $35 for two depending on what you order.

Barn 34, ocean side 34th Street – We’ve eaten here a handful of times for brunch, and everything we’ve tried has been great. Kim especially likes the Crab Benedict, which is a very rich take on Eggs Benedict made with Maryland crab meat. I typically order some type of omelette which are always tasty. The best part of this restaurant is its converted-barn atmosphere, though you probably want to avoid a window seat in the Winter because it gets chilly by the exterior walls. They’ve done a great job decorating the place. We’ve not tried Barn 34 at night, but they do have an upstairs bar that looks like it could be a great place to hang out.

Layton’s, ocean side 92nd Street and bay side 16th Street – We’ve eaten at Layton’s a handful of times with no complaints. They serve traditional breakfast foods–eggs, omelettes, french toast, pancakes, etc. as well as some lunch items. Their service has always been pretty quick and we rotate them into our restaurant choices occasionally. Price for two runs around $25.

Snack & Desserts

Thrashers, ocean side at the Inlet on the boardwalk – If you ask any Marylander who makes the best french fries at the beach, you’ll hear one answer: Thrasher’s. This place has been converting potatoes into awesome since 1929 and if there’s one thing you need to try before leaving the island, it’s Thrasher’s french fries. We like them topped with salt and vinegar. Thrashers also keeps old bay, ketchup and mustard handy. We’re constantly amazed at the following this potato joint has – there is nearly always a line even well into October when crowds subside.

Dumser’s Ice Cream, bay side at 49th and 123rd Street – Dumser’s has been operating in O.C. for decades. We don’t tend to get ice cream when Kim and I are traveling alone, but when we have the kids we’ve gone here a few times. Their ice cream is really good, but expect to pay resort prices. For our family of seven that means around $30 for ice cream. Instead, we usually just pick up ice cream and cones at the store and make our own.

Fisher’s Popcorn, boardwalk at 2nd Street – Second only to Thrasher’s as an Ocean City tradition, Fisher’s has been making the world’s best caramel popcorn since 1937. Seriously, this is the best popcorn anywhere. The key to fisher’s is to eat the popcorn when it’s still very hot and melts in your mouth, that’s when it’s the best! You can pick up a large tub of fisher’s for around $12.

Attractions for Families – Things We Like To Do

Free and Nearly Free

  • The Beach: This is why people come to Ocean City. O.C. is home to seven miles of the best public beaches in the mid-Atlantic. They are cleaned nightly and no section of the beach is off-limits to visitors, which means you can take a tour of the entire island just by walking up and down the beach. As we noted in our Where to Stay section, we think a direct oceanfront place is the best way to stay in O.C. if you can afford it.
  • The Ocean: The Ocean is warm enough for most people to swim from July through September. Life guards are in the chairs from Memorial Day through the first Sunday of Fall, usually around Sept. 21.
  • The Boardwalk: Ocean City’s iconic boardwalk stretches from the Inlet (before 1st Street) through 33rd Street and is one of the longest solid wood boardwalks in the U.S. During peak season, the lower streets that have the bulk of the rides, arcades, restaurants, and shops tend to get very busy, but honestly, the crowd is its own kind of fun. Street performers are allowed at each intersection where a street meets the boardwalk (about every 100 yards or so). Perennial performers include spray paint artists, sand sculptors, clowns, and one-man-bands. At the base of the boardwalk you’ll find Thrasher’s french fries, a must-try if you’re new to Ocean City.
  • Northside Park (125th Street): Home to the Winterfest of Lights from Thanksgiving to just after New Years, Northside Park is O.C.’s largest walking park. It also has great views of Assawoman Bay and a few sports fields where local teams play. Fireworks are launched here to celebrate Fourth of July and New Year’s Eve.
  • 94th Street Playground & Courts: On the bay side at 94th street next to the water tower is a playground with basketball and tennis courts. There is also a dog walking park here that can be used free-of-charge.
  • Assateague Island (National Seashore and State Park): Assateague Island is home to Maryland’s famous wild horses and is one of the more unique places near O.C. There is a small fee for guests to enter the actual park, but once inside you can see the horses up close. There is also a visitor center outside the gate that provides history about the park. Our family loves the National Park’s Junior Ranger Program, and Assateague Island does offer a badge if you complete their workbook and show it to a ranger.
  • Ocean Pines Skate Park: Located about 3 miles west of Ocean City just off of route 90 is the Ocean Pines community. Ocean Pines’ recreation center has an outdoor skate park that is free. Our boys describe it as “legit”. You have to fill out some quick forms at the front desk to get a sticker that goes on your kid’s helmet, which must be worn while in the park. Ocean City also offers a pay-for-use skate park that is bigger and has more ramps on the bay side of 3rd street. If you’re family has avid skaters, it might be worth the cost of a day pass (around $20).
  • The Salisbury Zoo: This zoo is located about 40 minutes west of Ocean City in Salisbury, MD. Even though the zoo is small, it’s free and it dubs itself the “Best Little Zoo in America”. Kim’s taken the kids here several times and they thoroughly enjoyed it.

Free things we still haven’t tried: 94th Street Arts Center.

Less Expensive Attractions

  • Inlet Rides: Located at the base of the boardwalk, the inlet rides operate carnival-style where you buy tickets to ride individual rides. We have this filed under “less expensive” because you can choose to limit your riding and get out for under $10 per person. If you ride a lot of rides, the cost can add up fast.
  • Boardwalk Tram (Inlet & 33rd Street): In the on-season you can ride the tram from one end of the boardwalk to the other. Round-trip tickets are $6 per person. You can pickup the tram at the inlet or at 33rd street. If you’re only visiting O.C.’s boardwalk once this can be a good way to quickly see the whole thing.
  • Marty’s Playland Arcade (Inlet): Our kids love this place and so do we. Marty’s is an icon at Ocean City offering skee ball, claw machines, air hockey, pin ball, and dozens of “ticket” games. We typically split $20 among our 5 kids so each of them gets 16 quarters to work with. That $20 buys about 1/2 hour of fun. Bonus: From November to March Marty’s offers free coffee and hot chocolate for parents.
  • Ripley’s Believe It or Not & Mirror Maze (Inlet): If you’re into weird stuff, Ripley’s can be a fun place to walk through. They’ve collected strange items from around the globe and brought them to O.C. Ripley’s also has a mirror maze that Kim and I did when we were down without the kids. It’s actually a ton of fun and at first very disorienting. Warning: Anyone in your group who is claustrophobic or has sensory issues should probably skip the mirror maze. It’s loud and over-stimulating inside. If you pay for the museum and the maze together you get a small discount.
  • O.C. Skate Park (bay side at 3rd street): If your kids are into skateboarding, the O.C. skatepark offers day passes for visitors. See our Free and Nearly Free attractions for an alternative skate park that is 3 miles west of O.C. and 100% free.
  • Miniature Golf (up and down Coastal Hwy): Ocean City is literred with various themed mini-golf places. Each one offers a unique twist on the game. The cheapest we’ve found is a simple course attached to the Grotto Pizza at 124th street. During the off-season games run just $5 per person. Indoor miniature golf is available 133rd street bay side.

More Expensive Attractions

  • The Slingshot (Inlet): This two-person launch ride is located at the base of the boardwalk with the other rides. But it costs $20 per person to ride or $50 for two people, t-shirts, and a video. It is an amazing thrill – it feels like you are launching into space. I rode it about five years back and once was enough!
  • Baja Amusements (Go Carts) (Route 50, West Ocean City): Every year after our homeschooling ends we reward the kids for their hard work with a trip to the Baja Go-Karts. Baja offers seven total courses, three of which are open to children at least 8 years old and the remaining open to everyone over 12. We try to go in May just before the big crowds arrive. Wrist bands are $35 per person and includes go carting, batting cages, a climbing wall, bumper boats, and more. Baja offers a $3 off coupon, but you must print it from their website before you arrive. This is one of our kids favorite activities, but due to the high cost we only go once per year.
  • The O.C. Rocket (Inlet, bay side): The O.C. Rocket is a jet boat tour that leaves from Assawoman Bay south of 1st Street and goes through the inlet out to the Atlantic. It tours most of Ocean City’s coast – from 1st through approximately 115th street, before turning around and coming back. The total tour is about 30 minutes long. We recommend not eating immediately before the ride as it definitely is rocky, especially on higher-wind days.
  • Boat and Jet Ski Rental: A number of places offer boat and jet ski rentals. I’ve tried both on different guys’ weekends throughout the years. Assawoman Bay is an excellent bay for shallow-water boating when the weather is nice. When the wind is down you can get up plenty of speed to pull tubes, or you can relax on a pontoon boat. Prices start at around $60 per half hour for jet skiing and you can typically get 2 people on each ski.
  • Jolly Roger Amusement & Water Park (30th Street): We haven’t taken our kids here yet, though it was one of my favorite places to go when I was a kid and is the largest single paid attraction at O.C. Jolly Roger is more of a traditional all-you-can ride amusement and water park where you pay to get in and then can spend the day there. While we enjoy amusement parks, we usually get our fill with other parks in the region.

Expensive things we haven’t tried: Parasailing, LaserTron on 33rd Street

Special Events

In recent years, Ocean City has worked hard to attract guests in the off-peak season with many weekend events and activities designed to coax people to the shore. O.C. now offers special events most weekends from March through October and a holiday festival that runs from Thanksgiving to the New Year. Events change weekends from one year to the next, and the best and most complete resource is the town’s calendar of events. Here’s a few of the events we’ve tried and enjoyed as a family.

Auto Enthusiast Events

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  • Cruisin’ / Endless Summer Cruisin’ (May & October) – Weekends featuring classic cars, historic cars, and basically the chance to show off or drool over the best cars from the last century.
  • Bike Weekend (September) – Typically on the first weekend after labor day, Bike Weekend brings more than 10,000 motorcycles to Ocean City. If you’re into bikes, it’s harder to see more of them in one place than you will here on bike weekend.
  • Corvette Weekend (October) – Literally thousands of Corvettes from the 1950s to the 2000s descend on Ocean City for three days in October. If you love America’s sports car, you’ll love this weekend.

Holiday-Themed Events

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  • Winterfest of Lights (Thanksgiving to Christmas) – Every year from Thanksgiving to Christmas, Ocean City converts Northside Park (bay side 125th Street) into a winter wonderland. The town brings the trams from the boardwalk up to the park and they take guests on a tour through more than 500,000 Christmas lights. Santa makes an appearance every evening between Thanksgiving and Christmas, and the covered tent offers cookies and hot chocolate for purchase, along with a little gift shop. Our kids really like this event and we’ve gone for the last two years.
  • New Years’ Eve Fireworks – For the last few years O.C. has added fireworks starting at midnight on New Year’s Day at Northside Park. Because it’s typically very cold on Dec. 31 in Ocean City, this event never gets too crowded, though we think at least 1/3 of the people in the city at the time come to it. We’ve managed to leave our condo at 11:30 and still find a place to watch the show. Fireworks last for about 20 minutes.
  • Fourth of July Fire Works – Ocean CIty holds municipal shows at two locations, Northside Park (bay side 125th Street) and on the beach at Division Street. Shows start at 9:30 and get very crowded. So plan to arrive no later than 8:00 to get a seat, and if you want a great seat you might consider showing up at 6:30.
  • St. Patrick’s Day Parade – Ocean City turns green on St. Patrick’s day with a parade down Coastal Highway. Most of the bars and restaurants that close for the winter open up starting on St. Patrick’s day.
  • SunFest – On the last weekend of the summer Ocean City hosts SunFest to celebrate the end of the season. There are arts and crafts for sale at the inlet under big tents and concerts at the Convention Center.