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🍦Who has the best cheesesteak in Annapolis?

🍦Who has the best cheesesteak in Annapolis?

Kurt Buddy, blast from the past, bridal icon moves after 43 years...

Naptown Scoop
August 20, 2025

TOGETHER WITH

Good morning, Annapolis. On this day in 1920, what later turned in the NFL was formed as the American Professional Football Conference. It only took 44 more years for the Buffalo wing to be invented. And who knows how many more years it will take for the Buffalo Bills to win a Super Bowl.

In today’s Naptown Scoop:

Kurt Buddy is dog of the week
Blast from the past
Bridal icon moves after 43 years

Let’s get to it.

— Lauren Burke Meyer, Dylan Roche, & Duffy Perkins

Bridgeview Estate: A Chesapeake Bay Masterpiece of Luxury & Elegance

There are homes, and then there are estates. Bridgeview, set on 18 private acres overlooking the Chesapeake Bay, isn’t just one of the finest homes near Annapolis — it’s one of the most extraordinary in Maryland.

This 20,000-square-foot residence features 8 bedrooms, 10 bathrooms, and commercial-grade construction. Designed for grand entertaining and daily living, it offers a seamless blend of elegance and functionality.

Step outside to breathtaking 180-degree Bay views, a heated pool and spa, a private sandy beach, and a pier with boat and jet ski lifts. Indoors, enjoy a theater, game room, gym and spa, and even a performance stage — perfect for hosting or relaxing.

Don’t miss this once-in-a-lifetime opportunity. Contact the Brad Kappel Team today to schedule your private tour of Bridgeview.

THE DIGEST

In case you missed it

The biggest (local) news from last week.

🕯️The Thomas Point Shoal Lighthouse is 150 years old.
📉 Several types of crime in Anne Arundel County are down double digit percentages vs. last year.
🚧 Annapolis is breaking ceremonially breaking ground on Robert Eades Park tomorrow.🎬 Good Morning American filmed in Annapolis last week.

Blast from the Past: Annapolis, 1939

Image source: Maryland State Archives “The Annapolis I Remember Collection”

Do you ever see a picture and vaguely recognize stuff — but at the same time, feel like you recognize nothing at all? That’s how we feel looking at this aerial shot of Annapolis from 1939. For those of us who are bad at math, it definitely wasn’t shot with a drone.

You’ll downtown Annapolis. Most apparent is the layout of the harbor along Spa Creek. Plus, landmarks: There’s the Maryland State House clearly visible in the distance, along with other landmarks like St. Mary’s Church and if you look really hard, Market House.

There’s also a much older Annapolis Yacht Club and a very different bridge into Eastport.

But it’s so. . . sparse. Annapolis wasn’t quite so developed as it is in 2025. Today you’re likely to see a lot more boats docked up at a harbor that has more marina infrastructure. And you might notice that Compromise Street has next to no traffic along it (sounds nice, right?).

Pictures like these make you realize there’s a balancing act at play between preserving historic charm, modernizing, and economic growth. And to be honest, we don’t envy the people with those jobs. But we do admire them.

Western Shore Veterinary Hospital offers your pets the finest wellness care, state-of-the-art diagnostics, dental treatment, and surgery ranging from spays/neuters to sophisticated treatments. You can find them online, by phone at 443-936-0660, or at 910C Bestgate Road, Annapolis, MD 21401.

Dog of the Week: Meet Kurt Buddy 🐾

Some of us thrive best when we have a task to do. It sounds like that’s definitely the case with Kurt Buddy, a 4-year-old Jack Russel mix who entered the SPCA in May. Volunteers describe Kurt as smart and possessing a high prey drive. In other words, he likes chasing squirrels (and toys that look like squirrels). He’s also loyal, having made friends with a few of the dogs he’s sharing the shelter with at SPCA. But even with the friends he’s made, he would do much better with a loving home with a human he could bond with forever. He might even be alright if you already have dogs at home. As long as he gets to meet them and sniff their butts first.

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LOCAL BUSINESS

Who has the best cheesesteak in Annapolis (according to you) 🧀 🥩

Y’all have some opinions on cheesesteak. According to Monday’s poll, Pip’s has the best cheesesteak in Annapolis. A solid choice no doubt. But personally, Bread & Butter Kitchen is criminally underrated here.

The write ins were strong with some hidden gems, dark horses, and bold opinions. Along with a few Philly transplants who claimed Annapolis doesn’t have any good cheesesteaks. We expected nothing less.

“Jeno’s in Severna Park. Second-generation family owned. Original owner was chef for head of the Naval Academy.” We saw a lot of Jeno’s in the write ins.
“Rocco’s is a huge miss on your list. It’s Rocco’s or Pip’s.”
“Cantler’s has a sneaky good cheesesteak.”
“South River Pizza in Edgewater. Validated by at least 3 Philadelphians. Proper overfilled roll, texture, everything.”

🎀✂️Cutting into the Future: Grand Opening of iCode Severna Park

This one’s for our tech-savvy kiddos (and future coders) ages 5 and up. iCode Severna Park is officially debugging boredom with a ribbon cutting on Friday, August 22, from 4–5:30 PM (ceremony at 4:30 PM). From coding and robotics to game design and AI, their STEM programs spark curiosity and innovation. Stop by the open house to explore hands-on classes and camps, gamified learning, and gadgets galore — think gaming computers, 3D printers, and drones. RSVP to the grand opening at 570 Benfield Rd.

Mary’s Bridal moves for the first time in 43 years 👰‍♀️

When a business spends 43 years in the same location, it can take you by surprise to realize they aren’t in the same spot anymore. But Mary’s Designer Bridal Boutique is still in business and serving the community, even if they’re no longer on Jennifer Road. To be honest, we’re not surprised a bridal business stayed in one spot so long. They’re bound to know a thing or two about commitment. Mary’s recently lifted the veil on the new store at 14 Annapolis Street, which founder and owner Mary Feeley described as a “must have” from the moment she walked through the commercial space. They’re open and available for appointments.

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.

Not Feeling Like Yourself Lately?

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It’s expert care, tailored to your body and your goals — with no guesswork and real results. Schedule your consultation today and start feeling like yourself again.

WHAT’S HAPPENIN’

Groundbreaking for Eades Park in Clay Street community

The City of Annapolis will ceremonially break ground on Robert Eades Park on Thursday with a ceremony celebrating the beloved resident and advocate for the Clay Street community. The park along College Creek will undergo an eight-month revitalization with bike racks, a water access path, a memorial circle with seating, and landscaping. Actual groundbreaking will be next month. 1:30 PM on Thursday, August 21.

Veterans Classic, season tix now on sale 🏀

Navy sports fans know that tickets can sell quickly, so it’s big news when tickets for the Veterans Classic — happening this year on Nov. 7 go on sale. As of this week, you can buy your tickets and snag the same seat for the Veterans Classic and every other basketball game this upcoming season. Individual game tickets will go on sale in October.

⛹️‍♂️ Who’s playing? The Veterans Classic on Nov. 7 starts with Tulsa vs. Rhode Island at 6 PM followed by Navy vs. Yale at 8:30 PM.

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.

EXTRA SPRINKLES

Ready, Set, Dink!

Clear your calendar — Annapolis Pickleball Club and Bay Capital Mortgage are bringing back the action at Truxtun Park. The 5th Annual Bay Capital Mortgage Open runs September 12–14, featuring singles, gender doubles, and mixed play for all levels. Registration is open now through August 31, and every entry helps support the SPCA. Don’t miss your shot at medals, bragging rights, and a weekend of non-stop pickleball. Registration is open now through August 31, and a portion of proceeds supports the SPCA.*

*indicates sponsored advertising content.

WEATHER

Wednesday

81 🌡️ 70 | 🌦️ | 47% | E 8 mph (7 knots)

Thursday

73 🌡️ 65 | ☁️ | 23% | NNE 16 mph (14 knots)

💧🌡️ Water temperature = 80ºF
Temperature readings taken from the mouth of the Severn River the night before publication

LIVE MUSIC LOWDOWN

Wednesday

Thursday

NAVY SPORTS

Upcoming games

Women's Soccer (2-0)
8/21 vs Wofford | W 2-0 | 5 PM

Men's Soccer (0-0)
8/21 vs. Mount St. Mary's | 8 PM

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THANKS!

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🍦Who has the best cheesesteak in Annapolis?

Kurt Buddy, blast from the past, bridal icon moves after 43 years...

TOGETHER WITH

SPONSORED BY BRAD KAPPEL
EXECUTIVE VICE PRESIDENT
TTR SOTHEBY’S INTERNATIONAL REAL ESTATE