We’ve got a busy week ahead of us. Although the famed annual U.S. Sailboat Show, followed by the U.S. Powerboat Show (see photos of the latter here), will be wrapped up as of today, there’s no break when it comes to all of Annapolis’ goings-on this season. 

Get in the Halloween spirit this weekend at the Halloween on the Avenue Festival or the Dogtoberfest Homebrew Festival, or by embarking on a spooky tour like the Sins & Secrets Tour at Historic London Town, or the “Historic Hauntings” Annapolis Ghost Tour. Otherwise, find entertainment in one of the many theatrical performances happening this fall, or at a Navy home game. The possibilities are endless… Find them all below.

Finally, if you’re headed to the Shore this weekend, you won’t be disappointed by all of Ocean City’s O.C.toberfest happenings. They start this weekend, and as always, they guarantee a howlin’ good time. 


An Exult of Pleasure: The English Passion for North American Plants — Thursday, Oct. 18, 6:30 – 8:30 p.m.

With over 30 years of experience and 14 years with Historic Annapolis as the former Director of Horticulture, Mollie Ridout will share her knowledge of gardening practices and historical and cultural landscape. Please join us for an informative lecture on late 17th century plant exploration in the Chesapeake region.

Halloween on the Avenue Festival — Sunday, Oct. 21, 10 a.m. – 5 p.m.

Annapolis Bootique District hosts their fun fall festival, Halloween on the Avenue Sunday, Oct. 21st 10am-5pm on Maryland Avenue and State Circle. This family-friendly event includes musical entertainment, a doggie parade, great shopping, and of course, tricks and treats! 

Walk to End Alzheimer’s — Sunday, Oct. 21, 11 a.m.

Held annually in more than 600 communities nationwide, the Alzheimer’s Association Walk to End Alzheimer’s® is the world’s largest event to raise awareness and funds for Alzheimer’s care, support and research. This inspiring event calls on participants of all ages and abilities to join the fight against the disease!

Annapolis Oyster Festival — Sunday, Oct. 21, 12:30 – 5 p.m.

Enjoy food, live music by local artists, unique crafts, face painting and demonstrations highlighting the vital role oysters play in maintaining the health of the Chesapeake Bay. Seafood lovers are invited to feast on raw and fried oysters, oyster stew, fried oyster roll sushi, cream of crab soup, Maryland crab soup, and much more. Hamburgers, hotdogs and homemade desserts will also be available. 

Dogtoberfest Homebrew Festival — Sunday, Oct. 21, 2 – 6p.m.

Dogwood Acres Pet Retreat and Annapolis Homebrew Club presents DOGTOBERFEST Homebrewing Fall Festival!

Spend the day with your pup sampling local home & craft-brewed beers, listening to live music, enjoying tasty food all while supporting a GREAT cause – Chesapeake K-9 Fund

Tickets include: admission, commemorative tasting glass, unlimited samples (21 and over) of exclusive brews from the Annapolis Homebrew Club, Charm City Meadworks and Buck Distributing Company (until the kegs run out!) , LIVE music by Bravenoise and 2 BOLD Chefs & a Mediterranean Truck & Catering will be there with TASTY gyros, burgers and MORE for purchase.

Navy Sports

Navy Women’s Volleyball vs. Lehigh University — Friday, Oct. 19

Navy Women’s Soccer vs. Colgate University — Saturday, Oct. 20

Navy Women’s Volleyball vs. Bucknell University — Saturday, Oct. 20

Navy Football vs. Houston: AAC Conference Game — Saturday, Oct. 20  

Navy Men’s Soccer vs. Boston University — Saturday, Oct. 20 

Who’s at Rams Head?

Monday, 10/15: The Greatest Love of All: The Whitney Houston Show Starring Belinda Davids

Tuesday, 10/16: JJ Grey

Wednesday, 10/17: Candy Dulfer

                                    Johnny Lang at Maryland Hall for the Creative Arts

Friday, 10/19: Full Moon Fever: One Night of Tom Petty and the Heartbreakers

Saturday, 10/20: Friends! The Musical Parody 

                                Ottmar Liebert & Luna Negra

More information and details about these shows can be found here

Recurring Events

Sins & Secrets Tour — Friday, Oct. 19, 6 – 8 p.m.

All new stories for 2018! Register early – the last two years sold out!

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! 

Ghost Tours Annapolis: Historic Hauntings — Oct. 19 and 20, 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!

James Brice Hardhat Tour — Oct. 20, 10:30 a.m. – 12 p.m.

Have you ever wondered what preservation in progress really looks like?  Take a peek behind the scaffolding at the James Brice House, where a major preservation effort is underway to restore the house to its 18th century grandeur.  Join one of our public tours to peer beyond the sawdust and learn about the people who built the house, lived and worked in it, and the craftsmen restoring it today.

Maryland Renaissance Festival — Saturday and Sunday — last weekend! — 10 a.m. – 7 p.m.

The Maryland Renaissance Festival is back for its 41st season! The festival includes 200+ entertainers, ten stages, a 3,000 seat jousting arena, 122 craft shops, 48 food and beverage emporiums, games, attractions and 85 acres of complimentary parking. Hang out with King Henry and his court in the 16th-century English village, Revel Grove and let merriment abound. 

Greenstreet Gardens Fall Festival — Oct. 20 and 21, 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. 21 and 21, 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. 21, 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.