Say So Long to Summer and Hello to Fall with these Awesome October Occasions!

2. Endless Summer Cruisin’
Oct. 4 - 7 Leave home in the rear view and cruise on down to Ocean City, Maryland October 4 - 7th for the 21st Annual Endless Summer Cruisin’ Ocean City. With over 2,000 hot rods, customs, classics, trick trucks, and more this is one exciting event you won’t want to miss. Meet at the Boardwalk, Oceanfront Inlet lot for the main event or make a pit stop at one of the many other Cruisin’ satellite locations spread throughout town. The 3-day Endless Summer Cruisin’ event will feature great giveaways, games, vendors, entertainment and more! For more information on this Endless event visit:

2. Family Bonfire on the Beach
Oct. 5 Break out your beach chairs and big cozy blankets because on October 5th families of all shapes and sizes are invited to enjoy a Family Bonfire on the Beach! Sit back, relax and indulge in an fine fall evening filled with s’mores, hot cocoa, refreshments, storytelling, and live music. From 6 - 8 pm at 130th street on the beach. Pre-registration is requested, but not required. Children under 16 must be accompanied by an adult. Ticket $$ are as followed: Youth - $3, Adult (over 18 years) - $5, and Families of 6+ - $15 flat rate. Leashed pets are welcome. Bonfire will be canceled in the event of inclement weather. For more information, contact Anna Duffey at 410-250-0125.

3. Corvette Weekend
Oct. 13 Are you keen on Corvettes? If the answer is yes, then meet us at the Inlet Lot and Clarion Hotel for the largest Corvette Club sponsored event on the East Coast. Free State Corvette Weekend kicks off October 13th and welcomes over 1,200 Corvette enthusiasts and owners. Attendees can enjoy car shows, road rallies, a parade and other related activities that benefit various charities. For more information, visit

4. Fall Restaurant Week
Oct. 14 - 28 Tempt your tastebuds during Fall Restaurant Week with these spectacular restaurant specials. Broaden your culinary horizons and explore places you’ve never been before or frequent your favorite participating hot spots. Enjoy special, fixed-price menus at unbeatable prices. No passes, tickets, or coupons are required. Simply choose a participating restaurant and dine out. For more information, visit

5. ACS Making Strides Against Breast Cancer 5K Run/Walk
Oct. 20 Big or small save them all! Raise awareness and funds to save lives from breast cancer at The ACS Making Strides Against Breast Cancer 5K Run/Walk! Admission fees for runners is $35 and all proceeds benefit innovative research, provide free information, and support local programs. Registration begins at 7:30 am at the Boardwalk and Inlet lot, enjoy live entertainment at 8 am, the run begins at 9 am, and the walk begins at 9:15. For more information, visit or call 410-749-1635

We can hardly contain our ex-FRIGHT-ment! O.C.Toberfest returns to Ocean City, Maryland October 20-21 & 27-28, 2018 for it’s seventh annual season! These spook-tacular, fun and free festivities will surely thrill the entire family!

6. Drive in Disguise and Halloween Parade
Oct. 20 Honk if you love Halloween at the Drive in Disguise and Halloween Parade. All are welcome to participate or to watch as Halloween decorated cars parade down the Ocean City boardwalk from 27th Street to the Inlet Lot. Vote for your favorite vehicle and after the parade head down to Caroline and Wicomico for some of the city’s best Trunk or Treating. Festivities begin at 3 pm, but prospective paraders must register and show proof of insurance in order to drive. For more information, call Nancy Howard at 443-235-4405 or email

7. Trunk or Treat
Oct. 20 Trunk or Treat your kiddos to an afternoon of candy collecting at the Boardwalk south of Caroline Street and north of the amusement pier as the Drive in Disguise gets parked and set up (or afterwards if you care to catch the display of spooky cruisiers. This sweet event begins approximately at 3:40pm and and will last as long as the participants have treats to give.

8. Howl-o-ween Pet Parade
Oct. 20 Dress up your furry friend and bring them to N. Division Street on the Boardwalk for a howl-of-a-good-time at the annual Howl-O-Ween Pet Parade. All animals are welcome to participate in this silly Halloween showcase. Sit back, relax and, cheer on your favorite 4-legged contestant. Every entry gets their moment in the spotlight; and the best dressed will be awarded wonderful prizes and surprises. The Howl-o-ween Pet Parade is free and donations of pet supplies and monetary donations will be collected to benefit the Worcester County Humane Society. Registration begins at 12 pm and the pageant begins promptly at 1pm.

9. Halloween Beach Maze
Oct. 20 - 21 and Oct 27-28 Ocean City’s Halloween Beach maze is one a-MAZE-ing experience you won’t want to miss. Children of all ages will enjoy this wonderfully wicked event full of spooky special guests such as witches, pirates of the sand, scary scarecrows, ghouls in the graveyard, zombies and more! This event is free and maze hours run 10 am - 5 pm on Saturdays and 10 am - 3 pm on Sundays. This event is FREE and full of twists and thrills!

10. Autumn Home and Condo Show
Oct. 27 - 28 Fall in love with your new home with help from the Autumn Home and Condo Show! This event is specifically designed for homeowners in all stages of remodeling, landscaping, and decorating their homes. Exhibitors will be on hand featuring a variety of merchandise, product demonstrations, and interior and exterior displays. This 2-day event will take place at the OC Convention Center; Saturday: 10 am - 6 pm and Sunday: 10 am - 4 pm. Admission: Adults: $6, Seniors (55 & up) and Students: $5, Kids 13 & under and Military, Police, and Fire with ID: FREE. For more information visit:

11. The Great Pumpkin Race
Oct 27 On your mark get set GO-urd! The fall fun continues with ““The Great Pumpkin Race” at N. Division Street and the Boardwalk. Build your own pumpkin race car to bring and compete in this wacky and zany, side-by-side, down-hill race or be a good seed and watch from the sidelines. A smashing good time for the entire family! Prizes will be awarded in each division, as well as for race car creativity. For a complete lists of event rules and specifics visit: or

12. Seaside 10-Mile & 5K Run
Oct 27 Rain or shine… a 5K run in the rain will do you just fine! Join in the 10-mile or 5K race, both beginning at the Ocean City Inlet. The race begins at 9 am and the course includes the world famous Ocean City Boardwalk! For more information visit

13. Swing for Youth Golf Open
Oct. 27 Fall is the perfect time for golf and ideal autumn weather makes for an even better Swing for Youth Golf Open event. On October 27, Eagle’s Landing Golf Course plays host to the OC Recreation Boosters 8th Annual Swing for Youth Golf Open. Participation is limited in this 4-person Florida scramble featuring an all-inclusive price of $125 per player, $500 per team. Price includes greens fees and cart, two mulligans per person, putting contest, “Tame the Beast”, and raffle tickets. The tournament begins with a shotgun start at 10 am. All proceeds benefit the youth programs of Ocean City’s Parks and Recreation. For more information visit:

14. Shore Craft Beer Fest
Oct 27 Celebrate OCtoberfest with friends and a couple of ice cold ones! On October 27th, 2018, from 12.30 pm - 4.30 pm meet us at Sunset Park overlooking the Assawoman Bay for the ever-awesome Shore Craft Beer Fest! Raise a glass to small-scale local breweries with BIG world-class taste. Enjoy live music, delicious beer, and a great party. For more information on The Shore Craft Beer Fest visit:

15. Halloween Spook-Out Party
Oct 28 Gather the little ghouls and goblins for an afternoon of Halloween fun at Northside Park’s Halloween Spook-Out Party! Perfect for participants of all ages, including parents, festivities include: carnival games, arts and crafts, hayrides, costume contests, and one bag of individually wrapped candy per child! 1 - 3 pm at Northside Park Recreation Complex, 125th Street. Pre-registration not required.

Between the perfect temperatures, variety of fall events, excellent deals and discounts; October is the perfect month to book a trip to Ocean City, MD! So what are you waiting for? Book a stay at the Monte Carlo Hotel Group today!