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Shops in Chestertown

Local shops, services, jobs, and Main Street news.

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57 places

★ What stands out · Places

Shops and services in Chestertown

Most cluster around High St. Best-loved first: neighbor reviews and photos, then local before chains.

Dollar Tree

Discount store · 711 Washington Avenue Ste. 19

Directions (667) 899-6590 Website ↗

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Houston's Dockside Emporium

Clothing store · 315 High St

Directions (410) 778-9079 Website ↗

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Redner's Warehouse Markets

Grocery store · 17 Washington Sq

Directions (443) 666-3151 Website ↗

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Subway

Sandwich shop · 834 High St

Directions (443) 282-0005 Website ↗

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Gabriel's of Chestertown

Flowers and gifts shop · 207 S Cross St

Directions (410) 778-2123 Website ↗

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Village House

Furniture store · 103 S Cross St

Directions (410) 778-5766 Website ↗

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See all 57 shops and services on the mapPlaces →

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More on shop & services in Chestertown

The full pages behind this topic, with the numbers.

ExploreShops58listed in PlacesOpen →ExploreErrands & services325listed in PlacesOpen →ExploreWork & commute20 minaverage commute · where people workOpen →

More of Chestertown’s guide

Out & about first, then everything else.

Out & about

♨Eat & drink47 ♧Parks, sports & recreation17 ✳Arts, culture & entertainment23 ◉Environment & nature2

Living here

▤Town hall & decisions17 ⟲Trash, recycling & yard waste ⌁Utilities & services ↗Streets, parking & getting around ⊕Safety & preparedness2 ✚Health & emergency care18 ⌂Housing & development35

People & community

▧Schools & learning26 ✿Kids & families ♡Pets & animals4 ◎Faith & community groups12 ☼Neighbors helping neighbors

Our town

◷History & heritage ◫Photos & town views

Facts, tips, places and posts come from Chestertown neighbors on TownTapestry; facts go live when two neighbors confirm them. Place listings start from Overture Maps and are corrected by neighbors. Numbers on the doors come from each page’s public sources.