June - September
Memorial Day weekend kicks off the Ocean City summer season. The days are long and hot and the suntan lotion is almost as sticky as the humidity. In June, you may have to spend part of your vacation dodging drunk packs of teenagers and college students here on senior week (this is technically true all summer, but June is when they’re thickest on the ground). Throughout the season, and especially around July 4 and Labor Day weekend, the OC is crowded, but it rarely feels claustrophobic. While the ocean provides a cool breeze, the mercury regularly tops 90 degrees, so drink lots of fluids (beer and margaritas don’t count). The water is usually cool enough to shock you, relative to the heat, but your body will quickly adjust.
October - March
Visiting Ocean City in winter isn’t as unappealing as you may think. Yes, it’s freezing, but small towns like Snow Hill and Berlin are postcard perfect, both in the snow and under Christmas lights, and bed-and-breakfast properties are that much cozier in the cold. Ocean City itself takes on a wild, windblown character when the water turns a steel-purple and the wind whips snow and salt over the dune grass. You may not get much sun, but there’s a stark, end-of-the-world emptiness to the place that is appealing to certain folks. The price of the seaside hotels drops precipitously, and with a little negotiating you’ll likely get great deals at B&Bs.
April - May
This is a funny time of year: There are days (especially in April) when it’s bitterly windy, rainy and generally nasty, and there are days when it’s so gorgeous you’d think heaven had broke out on the Eastern Shore. Be warned: Even on the sunniest days the water is going be bitterly cold at this time of year, although you’ll see hardy souls having fun splashing about. On the other hand, all the rides and food stands will (likely) be lines-free, and there may be no better time to explore local picturesque small towns.