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Places in Winchester Winchester’s downtown: 79 places in a five-minute walk 114 places in Winchester: 16 places to eat and drink, 9 shops, 5 things to do and 1 places to stay. Local spots first, with directions to every one.
All places
114
76 per 1,000 residents
Eat & drink
16
11 per 1,000 residents
Shops
9
3 gifts · 2 antiques
Things to do
5
1 arts · 2 landmarks
Places to stay
1
0.7 per 1,000 residents
What kind of places does Winchester have? Read from every listing. The page puts what stands out first.
★ What stands out · The map Where Winchester gathers 79 of Winchester’s 114 places sit within a five-minute walk of S Main St.
Eat & drink 16 Shops 9 Things to do 5 Places to stay 1 Errands & services 49 Community 34
79 places in a five-minute walk of S Main St 69% of Winchester’s places
Eat & drink 16 places to eat & drink 7 restaurants, 4 cafés & treats, 3 bars & breweries. Local spots first.
See all → 🍽️ Restaurants 7 ☕ Cafés & treats 4 🍺 Bars & breweries 3 🥕 Farms & markets 2
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Pizza restaurant · 15 S Arch St
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Pizza restaurant · 12 E Cross St
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Taco restaurant · 12 E Cross St
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Restaurant · 772 Old Route 36
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American restaurant · 764 Old 36
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See all 7 restaurants → ☕
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Ice cream shop · 27 S Main St
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Bakery · 35 S Commercial St
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Bar and grill restaurant · 15 S Arch St
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Bar and grill restaurant · 24 S Main St
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Bar and grill restaurant · 26 S Hill St
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Butcher shop · 9 E Market St
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Butcher shop · 342 W Cross St
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Shops 9 shops 3 gifts & boutiques, 2 antiques & vintage, 2 home & hardware. Local spots first.
See all → 🎁 Gifts & boutiques 3 🕰️ Antiques & vintage 2 🔨 Home & hardware 2 🎣 Outdoor gear 1 🏪 More shops 1
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Flowers and gifts shop · Market Street - North Side Square
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Antique store · 20 E Cross St
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Thrift store · 28 S Main St
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Nursery and gardening · 776 Old 36
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Hardware store · 47 S Main St
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Bicycle shop · 21 S Main St
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Discount store · 772 Old Rt 36
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Things to do 5 things to do 2 history & landmarks, 2 fitness & sports, 1 arts & culture. Local spots first.
See all → 📜 History & landmarks 2 🏋️ Fitness & sports 2 🎭 Arts & culture 1
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History museum · 110 E Cherry St
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Landmark and historical building
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Bowling alley · 50 S Hill St
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Art gallery · 11 E Market St
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Everyday 49 errands & services Groceries, gas, the barber, the vet, the bank.
See all → Community 34 schools, churches & public places Where Winchester learns, worships and gets things done.
See all →
Talk & tips Favorites, openings and closings from Winchester neighbors.
Town Square →
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What’s missing?
Not on the map yet. It may just be missing.
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What’s your favorite place to eat in Winchester? → A new spot opened (or closed) in Winchester → Which Winchester business deserves a shout-out? →
+ Know a place that’s not here? Neighbors add the spots maps miss. It takes about a minute.
Some place details from Overture Maps (CDLA-Permissive-2.0), checked against the Census town line. Places added by neighbors go live once a second neighbor confirms them. Spot a mistake? Open the place and tap Edit mode .
How we sort and count Each list puts neighbor favorites first (ratings and photos), then the most complete listings (a website, a phone number, a note), with local, independent spots ahead of national chains. Categories come from each place’s map category, so a café filed under “Shops” still shows up with the cafés. “A five-minute walk” is a quarter mile from the busiest spot on the map. Per-1,000 figures use the Census population.