TOGETHER WITH

Good morning, Annapolis. Denmark is considering banning social media for kids under 15. The prime minister says online platforms are “stealing our children’s childhood.” Personally, I vote we go back to the golden days as well (countless hours spent playing outside with an hour or so a day for the world’s best computer game – Roller Coaster Tycoon 2).

In today’s Naptown Scoop:

  • Tons of fall fun

  • AACPS Teacher of the Year

  • Most popular stories from this week

Let’s get to it.

— Lauren Burke Meyer, Dylan Roche, Duffy Perkins

P.S. Join a Starry Night for a great cause — learn more below.

Share the Warmth This Season

Cooler days are near and not everyone has a cozy coat to grab from the closet. Annapolis Mall is partnering with One Warm Coat to help change that.

From October 15 to November 30, bring your gently worn coats to the collection bin near Crate & Barrel. Every donation helps someone in our community stay warm this winter — no coat left behind.

It’s a simple way to make a big difference. Clean out your closet, drop off a coat, and spread a little warmth right here in Annapolis.

THE DIGEST

The biggest stories we covered this week

🏝️ Half of St. Helena Island (in Round Bay) is heading to auction on October 22. Starting bids are expected to be $1–1.9 million. Which is honestly . . . not bad?

🎃 This was probably the biggest story we covered this week. Get it? Massive real pumpkins (many over 1,000 pounds) have been placed all over downtown Annapolis. They’ll be carved into pieces of art on October 24.

⛵ The Kaye family sold the its classic Annapolis schooners Woodwind and Woodwind II to 59º North Sailing, an adventure sailing company whose owner was a deckhand on Woodwind almost 20 years ago.

🏨 The Village at Providence Point broke ground on a 350-door independent living community that’s been in the works since 2011.

Most popular stories of the week 🏆

Who’s up for 2025-26 AACPS Teacher of the Year?

AACPS have announced their long list of teachers up for this year’s Teacher of the Year Award, and with 88 educators from around the country, we don’t envy the folks that have to choose. That inspiring educator will then represent the county in the Maryland State Teacher of the Year competition, which is generally announced in September. Three AACPS instructors have won the prestigious award in the last eight years. To see the full list of amazing educators, click here. But as an aside from all of us at the Scoop, we think every teacher deserves an award. Thanks for being awesome.

📅 The winning Teacher of the Year will be revealed at the Excellence in Education Awards in April.

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NAPTOWN SCOOP LOCAL BUSINESS IS POWERED BY. . .

Foodie Friday: Savor the Open Air

Temps are finally not sweltering, so let’s eat (and drink) outside before winter sneaks up. Here are writer Lauren’s go-to spots for a meal with a healthy side of sunshine. Apparently not this weekend though 😞

🍻 1747 Pub Beer Garden: Behind Reynolds Tavern, the historic space once housed stables for William Reynolds’ traveling guests. Enjoy lunch, Happy Hour (Sun—Fri, 3—7 PM), live music, Sunday movie nights, and Tuesday evening performances by the Annapolis Shakespeare Company — all outdoors! They pour American and imported craft beers and love to spotlight Maryland brews.

🍕🍷 Vin 909: The Eastport winecafe’s front porch feels like home, and its idyllic back space is perfect for sampling one of their 40+ wines, or micro, domestic, and small batch beers. Every pizza is pure bliss. Tip: They sadly don’t take reservations, so line up before lunch at noon (Wed–Sat) or dinner at 5 PM. Closed Mondays.

🦀 The Point: Everything tastes better with a water view. Go with a crowd and order one of every appetizer, especially the Fried Pickles and Crab Dip. Trust us. Half-priced apps and drink specials (Mon–Fri, 3–6 PM) sweeten the deal.

🥨 Garten: Travel to Europe sans passport. Inspired by Germany and France, Garten serves cheese and charcuterie boards, kebabs, schnitzel, fresh veggies, housemade pastas, and pretzels. Their archway, greenery, and twinkle lights beckon.

🍔 Metropolitan: Rooftop views and farm-to-table menu make this spot a must. Grab a $10 Met Burger on Thursdays.

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.

🎅Ho-Ho-Ho Before Halloween??

Pumpkins are still on the porch, but it’s already time to deck the halls — and the Annapolis Symphony Orchestra is here to help you get in the spirit (the festive kind, not the spooky kind).

This year’s Holiday Pops spreads the magic across the county with three concerts: Maryland Hall on 12/19, Severna Park High School on 12/20, and Bowie State University on 12/21. There’s an evening show for night owls and two afternoon performances for anyone who doesn’t want to stay out late. Bowie State University Concert Choir joins the celebration for even more festive joy.

WHAT’S HAPPENIN’

What we’re up to this weekend

ALL WEEKEND

⛵️ Annapolis Sailboat Show | City Dock | See the latest and greatest in sailboats and all the swag and gear you need | 10 AM-6:30 PM Fri-Sat, 10 AM-5 PM Sun

SATURDAY

🖼️ Art at the Park | Quiet Waters Park | Enjoy the best in local art and music at this family-friendly festival | 10 AM-4 PM Sat-Sun

🎶 Naptown Vinyl Record Show and Vintage Market | Maryland Hall | Gather at Maryland Hall to dig through crates of vintage records and find that hidden gem | 11 AM-4 PM

📚 Greenfield Library Annual Book Sale | St. John’s College | Bring your tote bags and stock up on used books for low prices | Noon-3 PM

🐉 Dragon Fest | Eastport | Join the Annapolis Dragon Boat Club for an afternoon of fun, food, and music. | Noon-4 PM

MARKETS

🥕 Anne Arundel County Farmers’ Market | Parole | Products, produce, and meat from local farmers and artisans | Sat 7 AM-Noon, Sun 9 AM-Noon

🌾 Fall Field Market at Wildberry | Crownsville | Join Wildberry and other local small businesses for an outdoor market on the farm | Sat, 9 AM-Noon

🍎 Severna Park Farmer’s Market | Severna Park | More products, produce, and meat from local farmers and artisans | Sat, 8 AM-Noon | Only runs through October so time is running out!

FALL FUN

🎃 Friends of the Light House Pumpkin Patch | Annapolis | Find the perfect pumpkin as part of this tradition to raise money for the Light House Shelter | 2 PM-6 PM Thur-Fri, 10 AM-6 PM Sat-Sun

🎃 Great Annapolis Pumpkins | Downtown Annapolis | Check out the enormous pumpkins, ranging from 600 to 1,500 pounds, decorating the downtown area | All weekend

🎃 Harvest Bash | Arnold | Join the Providence Center for an Oktoberfest-themed fundraiser | Saturday 7 PM

🎃 Fall Festival Weekends at Homestead Gardens  | Davidsonville | Get a true farm experience with barn animals, hayrides, and pumpkin picking. | 10 AM-4 PM Sat-Sun

🎃 Fall Fun Day at Kinder Farm Park | Millersville | Pumpkin patch, hayrides, straw maze, face painting, and more. Gate fees suspended. | 10 AM-3 PM Sat

Admiral Cleaners needs coats!

Even though the weather forecast is just now starting to dip below 80 degrees on the regular, we all know fall and winter are coming. And every year, Admiral Cleaners runs a coat drive in October and November, collecting, cleaning, and distributing thousands of coats to those in need. If you have coats you’ve outgrown, please bring them to any one of Admiral’s four locations or reach out to setting up a pickup. Local businesses can also act as a collection site, with Admiral dropping off boxes to keep the coats until they can be picked up. So clean out your closet and make someone’s winter season a little warmer.

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.

CIVIL NEWS

City Council Meeting ⚖

The City Council holds its regular meeting this upcoming Monday at 7 PM at City Council Chambers (160 Duke of Gloucester Street, Annapolis), and it has a packed schedule. The meeting will start with a series of citations and other ceremonial items, including recognitions for the Annapolis Symphony, LGBTQ Affairs, Hispanic Heritage, and Fire Prevention Month. The City Council will also consider legislative action on the implementation of Annapolis Ahead Comprehensive Plan 2040, ADU requirements, and limitations on short-term rentals per blockface, among other items. See the full agenda. Submit your comments or sign up to give testimony here.

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EXTRA SPRINKLES

A Starry Night for a Brighter Future

Join Anne Arundel Young Life on Thursday, November 20, for their signature gala at the Fluegel Alumni Center, made possible by the Brian & Patricia Giese Foundation. Enjoy cocktails, a gourmet dinner, and exciting auctions — all in “Starry Night Chic” style. Proceeds support Young Life’s mission to reach local teens with hope, purpose, and community. Get your tickets here.*

*indicates sponsored advertising content.

WEATHER

Friday

65 🌡️ 57 | ⛅ | 8% | 💨 E 10 mph (9 knots)

Saturday

70 🌡️ 63 | 🌦️ | 35% | 💨 NE 11 mph (10 knots)

Sunday

66 🌡️ 58 | 🌧️ | 68% | 💨 NE 25 mph (22 knots)

💧🌡️ Water temperature = 70ºF
Temperature readings taken from the mouth of the Severn River the night before publication

LIVE MUSIC LOWDOWN

Friday

49 West | Mac Walter | 7–10 PM
Annapolis Smokehouse & Tavern | Sidewalk Sou | 8:30 PM
Blackwall Hitch | Dana B | 4–7 PM
Blackwall Hitch | ONO Band | 9–12 PM
Brian Boru | Aidan and Bryan | 7–10 PM
Captain’s Daughter | TBA | 5–7 PM
The Choptank | Fred Moss Music | 8 PM
Galway Bay | The Langer's Ball | 7–10 PM
Great Frogs | Daphne Eckman | 5:30–8:30 PM
Killarney House | SVV Duo | 7:30–10:30 PM
Libbey’s Coastal Kitchen | Dave Hawkins | 5–8 PM
The Lodge | Andy B | 8–11 PM
Market House | Faith & the Faithful | 7–10 PM
Market Space | SVV | 6–9 PM
Middleton Tavern | Moon Cherry | 10 PM
Mother’s Peninsula Grille | Chuck Defontes | 5–8 PM
Old Stein Inn | Alexander Peter's in The Biergarten | 7–10 PM
Pirates Cove | Kurt Gibbons | 7:30–10:30 PM
Rams Head On Stage | The Ocean Blue w/ Brian Tighe | 8 PM | Tickets
Rams Head Roadhouse | Boroy | 8 PM
Rams Head Tavern | Chris Sacks | 5 PM
Romilo’s Restaurant and Bar | Shift Work | 7 PM
Severna Park Taphouse | Three Beers Wrong | 7 PM
Stan & Joe’s Riverside | Kevin Lebling | 3–7 PM
Stan & Joe’s Saloon | Racheal & The Rescuers | 9:45 PM

Saturday

49 West | Uptown Vocal Jazz Quartet | 8 PM
Blackwall Hitch | Samantha’s Duo | 9 PM
Brian Boru | Lauren and Rusty | 7–10 PM
The Choptank | Ciarán Quinn | 8 PM
Coconut Joe’s | JPARIS | 2–5 PM
Dark Horse | Timberwolves w/ Gatwick Band | 8:30 PM
Great Frogs | Ahmed Warshanna | 1:30–4:30 PM
Great Frogs | Guava Jelly | 5:30–8:30 PM
Killarney House | Brian Grumbine | 7:30–10:30 PM
Market Space | Brian Peacock | 2–6 PM
Middleton Tavern | Nate Finn Band | 10 PM
Mother’s Peninsula Grille | Sky King Duo | 8 PM
Pirates Cove | Jesse Moody | 7:30–10:30 PM
Rams Head On Stage | Close Enemies feat. Tom Hamilton | 8 PM | Tickets
Rams Head Roadhouse | Meerkat Nation | 9 PM
Rams Head Tavern | Emily & Chris | 5 PM
Romilo’s Restaurant and Bar | Wild Grey Hairz | 7 PM
Severna Park Taphouse | Red Betty & The Ruckus | 8 PM
Stan & Joe’s Riverside | Tim Atkinson | 3–7 PM
Stan & Joe’s Saloon | Viands & Co | 9:45 PM

Sunday

49 West | Hot Funyuns | 7:30–10:30 PM
Brian Boru | The Jazz Perpetrators | 4–7 PM
Galway Bay | The Corkers | 4–8 PM
Great Frogs | Dirk Schwenk | 1:30–4:30 PM
Market House | Laura Brino | 5–8 PM
Market Space | Brandt Dunn | 2–6 PM
Old Stein Inn | The Prost Polka Partei Band | 2–5 PM
Pirates Cove | Kevin Lee | 3–6 PM
Rams Head On Stage | Steven Page | 1 PM | Tickets
Rams Head On Stage | Technicolor Motor Home | 8 PM | Tickets
Stan & Joe’s Riverside | PJ & Neal | 3–7 PM
Stan & Joe’s Saloon | Simba | 9 PM

Upcoming games

Football (5-0)
10/11 @ Temple | 4 PM

Women's Rugby (3-2)
10/11 vs. Quinnipiac | 11 AM

Women's Soccer (8-5-1)
10/10 vs. Army | 4 PM

Men's Soccer (3-5-4)
10/10 vs. Army | 7 PM

Women's Volleyball (6-9)
10/10 vs. Colgate | 6 PM
10/11 vs. Bucknell | 6 PM

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THANKS!

Thanks for reading Naptown Scoop today. If you found something useful, please share it with someone you played Roller Coaster Tycoon with as a kid.

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