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🌱 How close were the Shoremen to a dramatic Chestertown comeback?

Chestertown, Maryland Patch AM: a 4 min read

Hey hey Chestertown! Your one-stop source for local news is here. Continue reading for all the updates. ☕️️

In today's newsletter:

  • How close were the Shoremen to a dramatic Chestertown comeback?
  • Chestertown joins Maryland’s $32 million push to cut child poverty
  • Thinking about retiring in Chestertown? See why it stands out

Also on today's calendar: Upper Shore Decoy Show and 9 more events.

Today's riddle: What has a cap but no head? 🤔 (Answer below!)

Weather forecast:

  • Saturday: A passing morning shower, with a high of 70 and low of 60 degrees.
  • Sunday: Rain most of the time, temps: high: 66, low: 60.
  • Monday: Partly sunny and pleasant, with a high of 74 and low of 49 degrees.

📰 News we're reading

• Shoremen Rally Falls Short Against Diplomats (washcollsports.com) — Washington College’s men’s soccer team narrowly lost 2–1 to Franklin & Marshall in Chestertown, despite a late first career goal from Gallo that nearly sparked a comeback. The Shoremen generated pressure all night at Kibler Field but couldn’t find an equalizer, and now turn their focus to a road conference matchup at Haverford on Saturday afternoon.
   

• Montgomery County Communities Included in Record $32 Million Maryland Child Poverty Initiative (mocoshow.com) — Chestertown is being added as a new community in Maryland’s $32 million ENOUGH Initiative, which targets child poverty with support for local programs in areas of concentrated need. While the article highlights Montgomery County examples, it confirms Chestertown will share in expanded state-backed investments aimed at improving economic mobility, education, healthcare, and food access across participating communities.
   

• The Best Small Towns To Retire In Maryland (worldatlas.com) — Chestertown is highlighted as one of Maryland’s best small towns to retire, praised for its historic district, walkable downtown, and lively arts and college scene along the Chester River. The piece notes the Saturday farmers market at Fountain Park, independent bookstores, and cultural events that make the town appealing to retirees seeking history, community, and riverfront charm.
   

📸 Around Chestertown

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🗓 Upcoming Events in Chestertown

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📣 Chestertown Shout Outs!

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💬 Chatter

What your neighbors are talking about on social media

  • Queen Anne’s County Government is proud to recognize three employees who recently graduated from the Academy for Excellence in Local Governance at the University of Maryland, along with a county employee who was recognized as an Academy Torchbearer.
    The 2026 graduation ceremony was held Sunday, September 27, at the Memorial Chapel on the University of Maryland College Park campus. A total of 124… (Nextdoor )
  • The Dixon Group posted a job opening for Welder - Hiring Now in Chestertown. Apply here.
  • Kentucky Fried Chicken posted a job opening for Team Member in Chestertown. Apply here. You can search for other jobs near Chestertown here.

🗞 Nearby News

Georgetown

  • As Peñalver Develops Strategic Plan, GU Community Hopes for Improved Policies (thehoya.com)
  • Bangbop Offers a Cruise Through Korea's Cuisine (thehoya.com)
  • Onstage Georgetown: October 2026 (georgetowner.com)

Aberdeen Proving Ground

  • Aberdeen Proving Ground Honors 'Soldier for Life' Ethos with 2026 Military Retiree Appreciation Day (army.mil)

Ok Chestertown! So now you're in the loop about what's happening today. Thanks for reading, and see you in your inbox next time! Oh -- and if you like what you're reading, invite a friend to Patch AM!

-- The Patch AM Team

P.S. The answer to today's riddle: "What has a cap but no head?" — A bottle (Thank you Glo M. for sending it in!)
Got a good riddle for PatchAM? Submit it here!

👉 Help make Patch AM better

We use a combination of real people and machines to tell you what’s happening around town. Learn more about Patch AM.

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Stay in the loop with what's happening in Chestertown

Never miss out on local news and events that matter to you.

Stay in the loop with what's happening in Chestertown

Never miss out on local news and events that matter to you.