Jack Frost has arrived… But don’t let that stop you from attending all the ghost tours, haunted hayrides and pumpkin patches begging to be visited this time of year. 

Save the Bay: Later this week, drivers will be able to purchase the newest Chesapeake Bay license plate that depicts a blue crab and the Bay Bridge. The plate is the third iteration of the bay-themed plate in 28 years, and will be available for $20 starting Oct. 29. 

Beer on the Beach at OCtoberfest: Take a mini-vacation this weekend: Ocean City’s biggest beer festival, Shore Craft Beer Fest: OCtoberfest is this Saturday in downtown OC’s Sunset Park. Enjoy unlimited tastings from 16 breweries, live music, shopping, food trucks and fun. Kids, pets and non-drinkers are free with a paying adult. Use the code “havefun” for $5 off each ticket. 😉 

Or if that’s too far away, treat yourself to a stay-cation in Annapolis and enjoy all the festive autumn fun going on this weekend. There are a few goings-on that your four-legged friends will be especially interested in…


Mr. Paca’s Backyard Preschool Program: Pumpkin Jack — Tuesday, Oct. 23, 10 – 11:15 a.m.

Grow pumpkin Grow! Come meet Pumpkin Jack and learn about the lives of Jack-O-Lanterns while exploring how pumpkins grow throughout the year. We will visit Mr. Paca’s Garden to explore the changes to plants and trees in the fall and make leaf people to decorate our homes!

Hammond – Harwood House Pumpkin Walk — Friday, Oct. 26, 4 – 6 p.m.

Join us for our annual Pumpkin Walk!!! The event will celebrate the season with games and a costume parade around the mansion. Kids will enjoy several fun activities and will learn about the architecture of the house. Witch telling stories, face painting, pumpkin toss, witch hat ring toss, popcorn and more. Cash bar for adults.

Sins and Secrets Tour — Friday, Oct. 26, 6 – 8 p.m.

Pirates, murder, and scandal aplenty await you on this adults-only, after-hours tour of Historic London Town and Gardens. Explore the dark underbelly of London’s history. Walk the streets of the long dead seaport, discovering its more salacious stories. Learn about exposed piracy, Scottish rebels, forbidden love, frozen fortunes and much more! 

Bark ‘n Dash 5k and Family Dog Walk — Saturday, Oct. 27, 9 a.m.

Kick off the Barkin’ Bash with a fun race through Quiet Waters Park! Well behaved and socialized dogs are welcome, but please be considerate of your fellow runners and keep your pet on a short leash near you. The Family Dog Walk is approximately one mile. Race day registration begins at 7:45 a.m., race begins at 9:00 a.m.

Corgi Howl-O-Ween Parade — Saturday, Oct. 27, 10:30 a.m. – 1 p.m.

Come hang out and participate in the costume contest and 50/50 raffle. This year we are raising money for East Coast Corgi Rescue, a non-profit organization based in DC that helps save corgis and corgi mixes in need up and down the East Coast, focusing on the mid-Atlantic region.

Navy Men’s Soccer vs. Colgate University — Sunday, Oct. 28, 12 p.m.

Come root for your favorite Navy team as they play Colgate University at the Glenn Warner Soccer Facility. Admission is free.

Who’s at Rams Head?

Monday, 10/22: Iris Dement

Tuesday, 10/23: Don Felder formerly of The Eagles

Wednesday, 10/24: Pokey LaFarge w/ The Watson Twins

Thursday, 10/25: Wynonna & The Big Noise: Roots & Revival Tour

Friday, 10/26: An Acoustic Evening with John Hiatt, The Eclipse Sessions Tour

Saturday, 10/27: Burlesque-A-Pades Halloween Spooktacular Featuring Angie Pontani

Sunday, 10/28: Melodies & Visions: Loving David Glaser Matinee Show

                             The Capitol Steps

More information and details about these shows can be found here

Recurring Events

Ghost Tours Annapolis: Historic Hauntings — Oct. 26 and 27, 7:30 – 9:30 p.m.

During the Month of October- Includes the Spooky Interior of a historic home. Exclusively available after hours to Annapolis Tours by Watermark’s guides and guests. Step inside and discover a ghost story of your own!

Looking for ghost tours in Maryland? This year instead of heading to the usual Haunted House full of unconvincing tricks, come with Watermark on a special haunted ghost tour of Annapolis during the festive month of October. Special Historic Hauntings takes guests inside one of Annapolis’ most notoriously haunted houses! Step back into time and hear the tales of the spirits that linger inside the dimly lit mansion. Only our ghoulish guides have access to bring you inside this haunted structure after dark. No visit to Annapolis is complete without seeking out the spirits!

Greenstreet Gardens Fall Festival — Oct. 27 and 28, 10:30 a.m. – 5 p.m.

Hay Rides • Jumping Pillow • Tire Tower • Corn Maze • Underground Slide • Corn Box, and Much, Much More

Homestead Gardens’ 35th Annual Fall Festival — Oct. 27 and 28, 11 a.m. – 5 p.m.

Celebrate Autumn at Homestead Gardens’ 35th Annual Fall Festival – the largest in the area!

With a wide array of attractions and entertainment for kids of all ages, your experience is sure to be an unforgettable one.
From our store, to the barnyard, through the corn maze and pumpkin patch, Homestead Gardens is alive with the colors of fall.

Sunday Outdoor Free Movies in the Garden — Oct. 28, 8:30 – 10:30 p.m.

First of all, who doesn’t love a Free Movie Screening? Add the fact that it is outside under the beautiful Annapolis sky, and you automatically have a family friendly, romantic, relaxed Sunday evening!

Every Sunday Night our Beer Garden becomes your Neighborhood Outdoor Movie Theatre with Free Classic Movie Screenings. All screenings are free and open to the public. Because all of our screenings begin at dusk, the start time may vary throughout the season.