Your sign to book a weekend trip to Chestertown, MD 📍 Save this to refer back to & send it to someone you’d like to get away with ✨ Chestertown feels like it’s straight out of a Hallmark movie. Just 1 hour from Annapolis, this cozy historic town tucked on the Chester River is the perfect destination for crisp fall strolls, charming cafes, boutique shops, fireside dinners, and golden leaves along the waterfront. 🍁 Stay at the @whiteswantavern or @bramptoninn 🍴Dine at @watershed_alley for eleva
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Your sign to book a weekend trip to Chestertown, MD 📍 Save this to refer back to & send it to someone you’d like to get away with ✨ Chestertown feels like it’s straight out of a Hallmark movie. Just 1 hour from Annapolis, this cozy historic town tucked on the Chester River is the perfect destination for crisp fall strolls, charming cafes, boutique shops, fireside dinners, and golden leaves along the waterfront. 🍁 Stay at the @whiteswantavern or @bramptoninn 🍴Dine at @watershed_alley for eleva
294 viewsOct 8, 2025
FacebookMichele Deckman
We’re thrilled to share our latest travel reel featuring Chestertown, Maryland, our first stop on a multi-day adventure through the Eastern Shore. From the moment we arrived, the town's charm captivated us. Its rich history, stunning Victorian homes, and vibrant downtown painted a picturesque backdrop for our journey. We loved exploring the waterfront and taking leisurely strolls through the historic streets. Chestertown is truly a hidden gem, offering so much to discover. Check out the reel and
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We’re thrilled to share our latest travel reel featuring Chestertown, Maryland, our first stop on a multi-day adventure through the Eastern Shore. From the moment we arrived, the town's charm captivated us. Its rich history, stunning Victorian homes, and vibrant downtown painted a picturesque backdrop for our journey. We loved exploring the waterfront and taking leisurely strolls through the historic streets. Chestertown is truly a hidden gem, offering so much to discover. Check out the reel and
2.4K views10 months ago
FacebookWanderers Compass Travel Blog
Visit Chestertown on Instagram: "Fall in Chestertown >>> 🍂🎃☕️🍎🍁 #chestertownmd #downtownchestertown #easternshoremd #chestertownlife #historictown #colonialtown #eastcoastlifestyle #pumpkins"
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Visit Chestertown on Instagram: "Fall in Chestertown >>> 🍂🎃☕️🍎🍁 #chestertownmd #downtownchestertown #easternshoremd #chestertownlife #historictown #colonialtown #eastcoastlifestyle #pumpkins"
10.2K viewsOct 7, 2025
Instagramvisitchestertown
Visit Chestertown on Instagram: "First snow of the season ❄️ happy snow day Chestertown! #chestertownmd #downtownchestertown #eastcoastlifestyle #eastcoaster #coastaltown #historictown #easternshoremd #maryland"
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Visit Chestertown on Instagram: "First snow of the season ❄️ happy snow day Chestertown! #chestertownmd #downtownchestertown #eastcoastlifestyle #eastcoaster #coastaltown #historictown #easternshoremd #maryland"
11.5K views10 months ago
Instagramvisitchestertown
Cat Janisko | Solo Travel and Lifestyle on Instagram: "Chestertown, Maryland is a historic port town that sits right along the Chester River. Once a major colonial trading hub, it played a role in early Revolutionary protests and still carries that history through its preserved buildings, brick sidewalks and waterfront views. This town was such a surprise. From the 1700s architecture to the antique shops and quiet riverfront benches. It’s small, but has great depth like many of our US small town
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Cat Janisko | Solo Travel and Lifestyle on Instagram: "Chestertown, Maryland is a historic port town that sits right along the Chester River. Once a major colonial trading hub, it played a role in early Revolutionary protests and still carries that history through its preserved buildings, brick sidewalks and waterfront views. This town was such a surprise. From the 1700s architecture to the antique shops and quiet riverfront benches. It’s small, but has great depth like many of our US small town
23.5K views8 months ago
Instagramunpackedwithcat
Holiday Magic and Winter Charm at Brampton 1860 - Chestertown, Maryland #chestertown #easternshore
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Holiday Magic and Winter Charm at Brampton 1860 - Chestertown, Maryland #chestertown #easternshore
520 views10 months ago
YouTubeBetter Living - Travel. Food. Home. Lifestyle.
Food, Wine, & Halloween Fun at Brampton 1860 - Chestertown, MD #maryland #halloween #hotel
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Food, Wine, & Halloween Fun at Brampton 1860 - Chestertown, MD #maryland #halloween #hotel
185 views11 months ago
YouTubeBetter Living - Travel. Food. Home. Lifestyle.
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Happy @sultanadownriggingfestival weekend Chestertown! The weekend when our little town shows off the ships of the past ⚓️⛵️ Tag us in your weekend pics 📸 @visitchestertown #downrigging #downriggingfestival #sultana #tallships #tallship #chestertownmd #downtownchestertown #chestertownlife #eastcoast #eastcoastlifestyle | Visit Chestertown
11 months ago
FacebookVisit Chestertown
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Sunrise Wake Up at Still Pond Chestertown Maryland
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OSCAR WINNING MOMENTS CHALLENGE 2026 🎬🏠 Hometown entry: #chestertown #maryland / #travelshorts
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Central Jersey events • september 11–13 👀 Looking for things to do in Central Jersey this weekend? There’s a witchy NJ Oddities night market, a scenic wine train, Victorian Day, the 1925 Phantom of the Opera with live organ, the Beach Plum Festival SO much more happening across Central Jersey. These are just our faves, find the FULL weekend event list on NJ Radar. 📍 #CentralJerseyEvents #ThingsToDoInNJ #NJEvents #NewJerseyEvents #CentralJersey
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