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
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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
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✨ Picture yourself stepping into Europe’s most exciting September events, from Georgian ballrooms to dazzling light shows and stadium cheers! 🎆 September is packed with unforgettable celebrations: walk through Regency England at the Jane Austen Festival, watch sheep cross Southwark Bridge, marvel at the Blackpool Illuminations, experience classical music magic at Last Night of the Proms, and catch high-octane NFL action in London. 💸 Smart Savings: Use code TK888 on the TrainPal app for smart s
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