TOGETHER WITH
Good morning, Annapolis. Benjamin Moore just revealed its Color of the Year 2026 is Silhouette AF-655. Yes, it’s a cozy fall color. We might’ve suggested Scoop royal blue. 💙
In today’s Naptown Scoop:
Out-of-towner wins $1M lotto
Positano teases us
What we’re looking forward to in November
Let’s get to it.
— Lauren Burke Meyer, Dylan Roche, Duffy Perkins

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THE DIGEST
$1 million lottery ticket in Annapolis 💰
We’ll start by saying this — it could’ve been you. It wasn’t though.
A $1 Million Royale scratch-off lottery ticket sold at Annapolis Wine & Spirits on Forest Drive. But not to a local. The lucky winner was a Virginia resident visiting Annapolis. She stopped by the liquor store before her drive home and impulse-bought the ticket. (Hey, she loves scratch-offs and couldn’t resist.) Even though the $1 million lottery winnings are going to an out-of-towner, Annapolis Wine & Spirits is still a winner too. They get a $1K bonus for selling the ticket.
BTW, the $1 Million Royale still has two $1 million tickets out there. Is this the part where we tell you to please play responsibly?
Blast from the past: Vintage Annapolis Yacht Club

We love this vintage shot of the Annapolis Yacht Club from 1963: the old building was destroyed in a fire in 2015, but here it stands in all its glory, overlooking Spa Creek. Fun fact: Wednesday Night Racing was started around the same time as this postcard’s publication - 1959 - with no prizes, no race committee, and no scoring. They did, however, enjoy a picnic lunch after sailing.
The new building was conceived by local architecture firm Hammond Wilson, who retained the iconic character of the original building, if you ask us.
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NAPTOWN SCOOP LOCAL BUSINESS IS POWERED BY. . .
Reader Recs: Best Soup Spot in Town 🥣
Fact: There’s no official start/end date for Soup Season. At Scoop, we begin when we won’t sweat while eating it wearing a sweater. Safe to say we’re in it (or at least close for those of us still sweating in the afternoon sun while dining al fresco). This is sure to be a heated two-parter debate . . .
What’s your favorite soup spot?
And, what are you ordering?
📧 Reply and let us know!
Positano teases us on Facebook
We mentioned back in August that we were thrilled to see Positano Ristorante & Pizzeria grab the gorgeous space formerly occupied by Agave in West Annapolis. Just thinking of authentic homemade pasta within walking distance makes the long winter that much more bearable. But will we have Positano here in time for the colder months? A recent update on their Facebook page reinforced the idea that the ball is still in motion, but since no official opening date has been announced, and our resident mole in the City Permits office came up empty handed, we’re still waiting. We’ll let you know when we have our Gnocchi Night Out on the calendar.
Italian restaurant Cavalli closes at Annapolis Town Center
Just about 4 months after opening at Annapolis Town Center, Cavalli announced in a brief social media post yesterday that it is now closed effective immediately. We’re unsure if the closure is related to the recent sale of ATC to Federal Realty or perhaps the loss of the parking lot across the circle which is being developed into a 175-unit active adult community. Either way, it’s been a sad week for local restaurants with 100 Lots in Edgewater closing over the weekend as well.
Nothing in this section is sponsored. They're just the things you need to know. I'll always let you know when something's sponsored.

WHAT’S HAPPENIN’
Theatre Talk Tuesday 🎭
🏫 Theatre Classes for All Ages Ongoing. Calling all performers (and aspiring performers) ages 4 to adult. Compass Rose Theater has fall classes and workshops. Enrollment is now open. Learn about musical theater, improv, play production, and acting.
🌥️ Compass Rose Theatre presents Annie Sep. 19-Oct. 26. The Compass Rose season begins with this family-friendly musical about a plucky orphan who knows the sun’ll come out tomorrow.
🧛♂️ Colonial Players presents Dracula: A Comedy of Terrors Opening Oct 24. This hilariously absurdist take on the classic vampire story may cause bloodcurdling screams — of laughter.
💔 Children’s Theatre of Annapolis presents West Side Story Opening Oct 24. Young lovers are caught between rival gangs in this musical set to open the new season at CTA.
🎼 Live Arts Maryland presents The Phantom of the Opera with live music Oct. 30. No, not the Broadway musical—this is the silent film starring Lon Chaney, and its musical accompaniment for the showing will be performed live by St. Anne’s Church organist Larry Molinaro.
Reminder: Ignite and Forward beer release
We’re doing a double cheers for tonight’s events (10/21). 🍻
IGNITE Annapolis: From activism to innovation, art to impact, local creatives and big thinkers get 5 minutes and 20 slides to share their ideas. The fast-paced event at Maryland Hall features cocktails and networking from 6 to 7 PM, followed by presentations from 7 to 9 PM. Tickets are only $10.
Beer for the Bay beer release party: Forward Brewing debuts its new crisp, golden blonde ale in partnership with the Chesapeake Bay Trust. Upgrade your license plate to a Bay Plate on site and snag 10% off your food at the Eastport brewery from 5–7 PM.
What’s Up, Witches?
Back for the fourth year in a row, this evening on Maryland Ave. promises all the magic of black cats and big hats to get you ready for Halloween. Businesses all along the Avenue are celebrating with spooky ghost stories from around Annapolis, tarot and astrological readings, bubbling cauldrons full of drinkable potions, and so much more. This is one of the best ghoul-friends events of the year, so round up the coven and get dressed up and ready to have some fun. Thursday, October 23, participating businesses on Maryland Ave. 5-8 PM.
What we’re looking forward to in November 🗓️
November is a busy month (hey, the holidays are coming up fast). Here are 11 events we can’t wait for:
🍷 Nov. 1: The 2025 Fish For a Cure Shore Party at Safe Harbor Annapolis brings together food, drinks, and dancing to fundraise for cancer survivors.
🇬🇷 Nov. 1–2: Get your Greek on at the Annapolis Greek Festival, where there will be Greek cuisine, live music, unique vendors, and all-around celebration of Greek culture.
🎨 Nov. 2: First Sunday Arts Festival returns along West Street for the final conventional festival in 2025. December brings the classic Chocolate Binge Festival. Don’t miss this day of shopping and entertainment before the monthly tradition goes on winter hiatus.
🪢 Nov. 8: Don’t miss the MRE Tug of War between Annapolis and Eastport. Usually held across Spa Creek, everything’s happening on Second Street in Eastport this year because of City Dock construction. The tug starts at the crack o’ noon and festivities continue throughout the day.
🏺 Nov. 9: Be there for the first-ever Naptown Flea Market in downtown Annapolis, featuring all kinds of vintage goods.
🥘 Nov. 9: The Inner West Street Association hosts the Taste of Fall, where you can sample the best of what local restaurants have to offer.
🏈 Nov. 12: The Anne Arundel County Hall of Fame induction banquet honors outstanding local athletes in a variety of sports with a ceremony at the Double Tree Hotel.
🍪 Nov. 22: Entries in the Great Annapolis Gingerbread Houses go on display at the Annapolis Visitors Center on West Street. (Winners of the contest are announced at the Annapolis Chocolate Binge Festival on December 7.)
💡 Nov. 23: Lights on the Bay opens its dazzling drive-through lights display at Sandy Point State Park (and runs through January 1).
🎄 Nov. 30: Close out Thanksgiving weekend with the Grand Illumination Tree Lighting in Downtown Annapolis, when the City Dock tree lights up for the first night of the season.
Nothing in this section is sponsored. They're just the things you need to know. I'll always let you know when something's sponsored.

WEATHER
Tuesday
70 🌡️ 53 | 🌤️ | 5% | 💨 S 13 mph (11 knots)
Wednesday
65 🌡️ 47 | 🌤️ | 11% | 💨 W 14 mph (12 knots)
💧🌡️ Water temperature = 64ºF
Temperature readings taken from the mouth of the Severn River the night before publication

LIVE MUSIC LOWDOWN
Tuesday
49 West | Unified Jazz Ensemble | 7:30–9:30 PM
Captain’s Daughter | TBA | 5–7 PM
The Point | Kavoossi | 5–8 PM
Wednesday
49 West | Dave Chappell & Friends | 5–7 PM
49 West | Gary Wright, Leah Weiss & Caleb Stine | 7:45–10 PM
Brian Boru | Nate Finn | 6–9 PM
Galway Bay | Irish Trad Music Session | 8 PM
Killarney House | Jason Bishop | 6–10 PM
Middleton Tavern | Johnny Poluos | 6–9 PM
Pirates Cove | Kurt Gibbons | 6–9 PM
The Point | Aaron Hawkins | 5–8 PM
Rams Head On Stage | A.J. Croce | 8 PM | Tickets
Rams Head Tavern | Shawn Owens | 4:30 PM
Stan & Joe’s Saloon | George Jano | 9:30 PM

Upcoming games
Men's Soccer (3-6-5)
10/21 vs. Longwood | 7 PM
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THANKS!
Thanks for reading Naptown Scoop today. If you found something useful, please share it with someone who already decorates their home in Silhouette AF-655.