TOGETHER WITH

Good morning, Annapolis. A woman just got 90 days behind bars for stealing over $15,000 of merchandise from Annapolis Mall. And that sounds like a lot until you learn it was all from Lululemon. By my math, that means she got away with six pairs of leggings and two of those trendy belt bags.

In today’s Naptown Scoop:

  • Lost stuffed kitty

  • Short-term rental forums

  • Up next at the Annapolis Summer Garden Theatre

Let’s get to it.

— Ryan Sneddon

Homestead for the Holidays 2026

We invite you to celebrate the season with us at Homestead Gardens as we welcome another year of Homestead for the Holidays, our annual celebration of tradition and community.

Join us November 6, from 6–9 PM, for our Annual Holiday Preview Party, featuring 25% off regularly priced items during the event. It’s the perfect opportunity to begin your holiday shopping and enjoy the season’s first festivities.

Throughout the season, we’ll welcome you back for our beloved train displays, photos with Santa, the Grand Illumination, Girls Night Out, and Santa Paws.

STRAND OFF

Tug of War Backstory: The March on City Hall 🪢

Every November, Eastport goes to war with Annapolis. Tug of war, that is. . .

It goes back to January of 1998. Allegedly, the State Highway Administration closed the Spa Creek Bridge for repairs. But the residents and business owners of Eastport saw right through the ruse for what it really was. . . a siege.

In response, they seceded from the City of Annapolis. In short order they drew up a constitution and national anthem and appointed a leader, barber Leon Wolfe. His Fourth Street shop (now home to a consulting firm) became the capitol.

That autumn, a multitude of Eastport-O-Ricans marched into a City Council meeting “nearly in tune with a trombone,” according to The Capital, and delivered a challenge to Mayor Dean Johnson. The first tug was set for November. And one of Annapolis’ most unique traditions was born.

Eastport residents wave Maritime Republic of Eastport flags around the podium at Annapolis City Hall

Photo: The March on City Hall 2026 by Glenn Miller

The Tug has endured many challenges. But perhaps none greater than the current construction at City Dock. The Maritime Republic of Eastport adapted, as it does. Like last year, all tugging happens on Second Street in Eastport.

Speaking of. . . this year’s tug is Saturday, November 7, at the crack o’ noon, and there are still 37 spots available on the public teams. Both the Annapolis Navy and Annapolis Bars are currently hopelessly outnumbered by their Eastport counterparts. Click here to sign up.

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EVENTS

Weekend preview

🎈 = family-friendly events

Thursday

👻 Chesapeake Ghost Stories Come to Life in Severna Park – Siren Theatre Collective brings Maryland ghost stories to life outdoors under the stars, with preshow tarot readings.

🎭 CP presents The Legend of Sleepy Hollow – Colonial Players stages Washington Irving’s classic ghost story with humor, suspense, and autumnal magic.

👻 Dark History of the South River – Evening tour of Historic London Town’s darker past, with tales of outlaws, fortunetellers, and 18th-century ghost stories.

🎨 Haunted Thrift Store Paint Night – Transform a thrift-store find into your own haunted masterpiece at ArtFarm, guided and beginner-friendly.

🎃 Die Laughing Presents: "Halloween Whodunit 3" – Interactive comedy murder mystery set at a horror movie casting call, with audience participation.

Friday

🎈👻 Halloween Story Time Parade – Kids parade in costumes from Edgewater Library to the senior center for spooky stories and treats.

🎨 Folklore & Folktales Exhibit Closing Reception – Final night to see this group show exploring folk art and storytelling, with artists present for conversation.

🛍️ Naptown Flea Halloween Night Market – Everything $40 or under at GameOn Bar + Arcade: vintage, secondhand, accessories, and local businesses.

🎈🎃 Pumpkin Walk 2026 – An Annapolis Halloween tradition at Hammond-Harwood House with games, crafts, storytelling, face painting, a costume parade, and mini mansion tour.

🧙‍♀️ Annapolis Witches & Legends walking tour – A 90-minute walk through Maryland’s colonial-era witch trials, superstition, and local legends.

Saturday

🎈🥕 Anne Arundel County Farmers Market – One of the biggest markets in Maryland, at Riva Road and Truman Parkway. Saturday 7 AM to noon, and back Sunday 9 AM to noon.

🎈🎃 Day of the Dead – Celebrate Día de los Muertos with live music, traditional dance, altars, art, food, and family activities at Chesapeake Children’s Museum.

🎈👻 Halloween Storytime & Parade – Gentle Halloween celebration for young kids with storytime and a costume parade at Eastport-Annapolis Neck Library.

🎈🎃 Homestead Gardens Fall Family Weekends 2026 – Final weekend of pony rides, hayrides, pumpkins, live music, barnyard animals, and inflatables in Davidsonville.

🍽️ Dinner Under the Stars: Motown Night – West Street puts the tables back in the street for one bonus night, with Spice playing Motown from 6 to 9 PM. Outdoor dining starts at 5.

🎭 Le Petit Masquerade @ Rumhouse – Elegant Halloween masquerade at a Caribbean restaurant with passed hors d’oeuvres, curated bar, and live rum experience.

Sunday

🎈🐝 First Sunday Market at Honey’s Harvest Farm – More than 30 vendors fill the farm’s historic barn in Lothian with produce, pasture-raised meat, seafood, wine, and craft beer.

🎈🥕 Anne Arundel County Farmers Market – Day 2 (see above)

🎨 First Sunday Arts Festival – Over 150 artisans, live music, and local food on West Street and Calvert Street.

🏛️ Honoring Maryland’s Emancipation Day at the Museum of Historic Annapolis – Guided tours on African American history, family crafts, and a children’s book nook; two tour times available.

🎈💐 Make a Memory Box for a Loved One – Hands-on session at Chesapeake Children’s Museum honoring the loss of a family member, friend, or pet; free for members.

More

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In other news. . .

🖌️ Seeing Red – Noticed the curbs downtown looking a lot redder this month? That’s because of the Ward One Residents Association. Their volunteers spent the month repainting faded no-parking curbs across Ward One. So far, 31 volunteers have gone through 43 gallons of traffic-red paint, most of it donated by Blue Star Painting.

🐱 Have You Seen This Cat? – A little girl dropped her stuffed cat on the way to the Navy game last Saturday. Her family thinks it happened near Taylor Avenue and Annapolis Street. He’s an orange tabby with a pink nose and white string whiskers, and he came all the way from Budapest. Keep an eye out. If you spot him, reply to this email and we’ll get him home.

🏘️ Rental Rules – Got opinions on the Airbnbs in your neighborhood? The city wants to hear them. Annapolis paused new licenses for non-owner-occupied short-term rentals for 12 months this spring, and now planning staff are asking how short-term rentals should work going forward. Take the survey, or tell them in person. There’s a forum at Pip Moyer Rec Center on November 4 and another at the Michael E. Busch Library on November 18.

🎭 Nice Work – Annapolis Summer Garden Theatre (ASGT) picked its first show of 2027. It’s the Gershwin musical "Nice Work If You Can Get It," running May 27 through June 19. The story follows a rich 1920s playboy and a bootlegger who hides her liquor in his mansion the weekend of his wedding. Also: ASGT needs a director! Proposals are due November 30. Apply here.

❄️ Cabin Fever Cure – Annapolis Recreation and Parks has opened registration for its winter programs. The Winter Program Guide has the full lineup of classes, sports, and camps at Pip Moyer Recreation Center, the Stanton Center, and Truxtun Park. Find us in the rock climbing, mahjong (so trendy), and LEGO engineers programs. Register here.

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WEATHER

Maryland’s Best Helmets & Harvest

Crisp fall weather calls for a day outside. Maryland’s Best Helmets & Harvest pairs local trails with farms, wineries and more through November 15. The free pass features stops like the BWI Trail, LEO Annapolis and other locations across the state. Check in at each stop to earn free prizes!

Thursday

68 🌡️ 53 | 🌤️ | 1% ☔ | 💨 SW 7 mph (6 knots)

Friday

73 🌡️ 49 | ☀️ | 0% ☔ | 💨 W 8 mph (7 knots)

💧🌡️ Water temperature = 63ºF
Temperature readings taken from the mouth of the Severn River the night before publication

LIVE MUSIC LOWDOWN

Residential Rug Care is a local family-run business with over 100 years of rug cleaning history. They clean Oriental, Persian, antique, and other area rugs, remove stains and pet odors, and offer new padding & fringe. Rugs are cleaned at their 20,000-square-foot facility, with free pickup and delivery throughout Anne Arundel County.

🌳🎵= Outdoor concert

Thursday

The Admiral’s Cup | Dan Heely | 7–10 PM
Beer Farm | Joey Fitz | 4–7 PM
Brian Boru | Ray Wroten | 6–9 PM
Copper Creek | Open Mic with Paul Cortese and Uncle Bill | 7 PM
Dark Horse | ilyAIMY | TBA
Harper’s Waterfront Restaurant | Aaron Hawkins | 7 PM
Killarney House | Anthony Broccolina | 6–9 PM
Market House | Doug Segree | 7–10 PM
Mother’s Peninsula Grille | The National Bohemians | 7 PM
Pirates Cove | Jason Bishop | 6–9 PM
The Point | Bryan Ewald | 5–8 PM

Friday

49 West | Sound of Presents: Lonesome October Vol 2 | 7:30–10 PM
The Admiral’s Cup | Nate & Jim Acoustic Duo, Fessup | TBA
Annapolis Friends Meeting | Peppino D’Agostino | 7–9:30 PM | Tickets
Annapolis Smokehouse & Tavern | Mixed Business | 8:30 PM
Beer Farm | Michael McHenry | 4–7 PM
Blackwall Hitch | Dana B | 4 PM
Brian Boru | Ciaran Quinn | 7–10 PM
Captain’s Daughter | TBA | 5–7 PM
The Choptank | Ryan Cobb | TBA
Coconut Joe’s | The Backburners | 4 PM
Great Frogs | Alexander Peters | 5:30–8:30 PM
Killarney House | Nicky Stacy | 7:30–10:30 PM
Market House | Ryan Moran | 7–10 PM
🌳🎵Market Space | Mike Sharp | 6–9 PM
Middleton Tavern | Local Soul | 10 PM
Mother’s Peninsula Grille | Devaney Bros | 8 PM
Pirates Cove | Faith & the Faithful | 7–10 PM
Rams Head On Stage | Crack the Sky | 8 PM | Tickets
Rams Head Roadhouse | Scott Hymes Band | 8 PM
Rams Head Tavern | Aaron Hawkins | 9 PM
Severna Park Taphouse | Dave Tieff | 7 PM
Stan & Joe’s Saloon | Deni Star Band | 9:45 PM

THANKS!

Thanks for reading Naptown Scoop today. If you found something useful, please share it with someone who still can’t wrap their head around the fact that they don’t have to manually change the time on their iPhone anymore.