Ghosts, Ghouls and Goblins Oh My! Halloween Happenings in and around OC

Where: Old Town Marina 307 Dorchester Street, Ocean City, MD 21842
When: October 2nd, 5:15pm OR October 9th, 5:15pm
Fee: $50
Tickets: OC Bay Hopper

Join OC Bay Hopper and Chesapeake Ghosts as you set sail on a haunted voyage of sightseeing and spooky ghost stories! Enjoy an OC sunset as you sail through Ocean City and Assateague aboard the Ocean City Spectral Voyage. 

Where: Windmill Creek Vineyard & Winery 11206 Worcester Hwy, Berlin, MD 21811
When: October 9th, 6pm
Fee: $33
Information

Put your cake decorating skills to work as you decorate three cupcakes at this 21+ Cupcakes and Wine event! All supplies will be provided, including the cupcakes and tools required to decorate 3 cupcakes. Food and beverages available for purchase from Windmill Creek and The Garden Grill. 

Where: Tides & Vine 106 West Green Street, Snow Hill MD 21863
When: October 15th, 6-9pm
Fee: $60.54 (incl. $5.54 fee)
Tickets: Eventbrite

Flex your painting skills as you create a Halloween-themed portrait of your pet! Submit your pet photo prior to the event, and the workshop artist will have a sketch with or without a Halloween costume ready to go for you to paint. If you’re not a painter, don’t worry, as no experience is necessary! 

Where: Forgotten 50 Distilling 10103 Old Ocean City Blvd, Berlin MD 21811
When: October 16th, 6-8pm
Fee: $39.19 (incl. $4.19 fee)
Tickets: Eventbrite

Experience a fun, hands on event with a Halloween-themed sugar scrub workshop from Simply Soft Sugar Scrubs owner Rachel Miller. Choose from a variety of autumnal scents including Hocus Pocus (Hot Apple Pie), Spooky Season (Harvest Moon), Caramel Pumpkin, and Campfire Marshmallow, and then create your very own sugar scrub. Don’t have experience? Don’t worry! Rachel will guide you through the process as you create your very own 11oz sugar scrub.

Where: 130th Street on the Beach, Ocean City MD 21842
When: October 18th, 6-8pm
Fee: $3 Kids, $5 Adults (over 18), with $15 max per family
Information

Head to 130th Street on the Beach on October 18th for a bonfire for the entire family! Enjoy the fall festivities with music, yard games, and more. Leashed pets are also welcome! Pre-registration is encouraged.

Where: 239 Ocean Parkway, Ocean Pines MD 21811
When: October 19th, 9am-12pm
Fee: Free
Information

On October 19th, spend your morning strolling through the Artisan Village as you enjoy fresh apple cider and select the very best pumpkins for your home! 

Where: Main Street, Berlin MD 21811
When: October 19th, 11am-4pm
Fee: Free
Information

Oktoberfest returns to Berlin as vendors from all over the area come together for Berlin’s Annual Sidewalk Sale, kids’ art, two stages of authentic Oktoberfest music, food, beer, a petting zoo, and more. Don’t miss this classic fall event!

Where: Fager’s Island 201 60th Street on the Bay, Ocean City MD 21842
When: October 19th, 12-4pm
Fee: $80.56 (incl. $2.56 fee)
Tickets: Ticket Leap

On October 19th, enjoy the Fager’s Island Fall Wine Fest. Taste a variety of wines from all over the world and enjoy live music from Groovalicious and DJ Robcee! There will be craft beer, oysters, and Fager’s Island dishes, and admission also includes a souvenir tasting glass.

Where: Roland E. Powell Convention Center 4001 Coastal Highway, Ocean City MD 21842
When: October 19th-20th, 10am-4pm
Fee: $6, Free for kids 13 and under and military, fire, and police (with ID)
Information

At this year's Autumn Home Show, there is fall fun for everyone! Throughout the weekend, kids can enjoy juggling lessons, games, magic, and more. They can also meet some of their favorite TV characters, like Bluey and Spongebob. 

The entire family can participate in costume contests, with categories including scariest, funniest, most creative, and best group/family. 

While the kids play, the Autumn Home Show is great for parents to learn about home services. The Art and Craft fair will offer a variety of vendors and is perfect for finding unique gifts! 

Where: Windmill Creek & Winery 11206 Worcester Hwy, Berlin, 21811
When: October 22nd, 6-8pm
Fee: $33.85 (incl. $3.85 fee)
Tickets: Eventbrite

Get into the autumn spirit with your very own whimsical pumpkin painting! Join artist Jessica L. Schlegel at Windmill Creek on October 22nd to learn how to paint your own canvas. Food and beverages from Windmill Creek and The Garden Grill available for purchase.

Where: The Modern Graze 36298 Old Ocean City Road, Willards, MD 21874
When: October 24th, 5:30-7pm
Fee: $39.19 (incl. $4.19 fee)
Tickets: Eventbrite

If your kiddo loves a good array of snacks, the Charcuterie Tricks-N-Treats is for them! In this workshop, kids will enjoy a hands on Halloween charcuterie board making class as they put together their own spooky snack boards. Everything your child needs to create their board will be provided, in addition to Halloween treat bags and juice boxes. For extra fun, costumes are encouraged! 

Where: Reverie Arbor & Wine Bar 7 South Main Street, Berlin MD 21811
When: October 24th, 7-9pm
Fee: Free
Information

It’s not Halloween without spooky ghost stories. Join Chesapeake Ghosts’s tour guide Mary at Reverie Arbor & Wine Bar in Berlin as she shares spooky stories and invites attendees to share their own as well! 

Where: Stephen Decatur Park Tripoli Street, Berlin MD 21811
When: October 25th, 7-9pm (Rain date October 26th)
Fee: Free or $25 to sponsor a pumpkin
Information

Enjoy a display of individually carved jack-o-lanterns as you stroll through Stephen Decatur park! This event is great for the entire family, and proceeds benefit Berlin gardens. A $25 donation allows you to participate and display your own pumpkin. With your donation, the pumpkin and glow light are provided. All ages welcome, and candy collecting bags, costumes, and flashlights are encouraged!

Where: 235 Ocean Pkwy, Berlin MD 21811
When: October 25th & 26th, 7:30-9:30pm
Fee: $8
Information

It’s back! Once again, the Ocean Pines Haunted House is bringing some spooky fun to the town. For two nights, make your way through the scares of the house as you have a spooky good time!

Where: Stephen Decatur Park Tripoli Street, Berlin MD 21811
When: October 26th, 10am-1pm
Fee: Free
Information

For any kiddos with an affinity for fire, garbage, and utility trucks, the Touch a Truck-N-Treat is a must-attend event! On this fun day, kids will get to learn all about their favorite trucks while receiving treats as well. Costumes encouraged! 

Where: Ocean City Boardwalk at 698 N Atlantic Ave, Ocean City MD 21842
When: October 26th, 1-3pm (Rain Date: October 27th, 11:30am)
Fee: Free
Information

Grab a spot along the boardwalk to watch the annual Howl-O-Ween Pet Parade! Part of Sunfest, this event brings in dogs from all over the region as they compete in a parade for the best Halloween costume. It’s a fun filled event perfect for the entire family. After the parade, be sure to head into Sunfest for even more fall activities! 

Where: Fenwick Inn 13801 Coastal Hwy, Ocean City MD 21842
When: October 26th, 5-11pm
Fee: Free
Information

Compete for awesome cash, gift card, and hotel stay prizes when you come dressed in costume to Fenwick Inn’s Halloween Costume Contest! Enjoy live music, food and drink specials, and more at this fun Halloween event at the Lookout Loft.

Where: 9913 Seahawk Rd, Berlin MD 21811
When: October 29th, 6-8pm
Fee: Free
Information

The NEHS and SDHS annual trunk or treat is back for its third year. Clubs and organizations will be set up in decorated booths throughout Stephen Decatur, allowing attendees to grab treats and more! Wear your favorite costume for a fun event benefiting Worcester County Public Libraries. 

Where: Roland E. Powell Convention Center 4001 Coastal Hwy, Ocean City, MD 21842
When: October 31st, 4:30-7pm
Fee: Free with costume
Information

A costume grants you free admission to the Haunted Highway: Trick-or-Treat Bash! This event takes place during the OC RV & Van Lifestyle Show. As kids move throughout the convention center, they’ll be able to trick-or-treat by going to the various RVs, vans, and exhibits at the show. 

Where: Downtown, Berlin MD 21811
When: October 31st, 5-7pm
Fee: Free
Information

On Halloween night, head to downtown Berlin for spooky festivities and trick-or-treating! This year’s theme is Dia de los Muertos. Wear your best costume and head out for a night of exploring the town!