Best of Chestnut Hill

by Cuppy

Top picks from across the web in Chestnut Hill.

Here's the plan

Seasons 52

Seasons 52

220 Boylston St Bldg. C117, Chestnut Hill, MA 02467$$

🇺🇸 American🍸 Bar🍽️ Casual🎵 Live Music🌞 Outdoor Seating🍷 Upscale

Rotating menu of seasonal American dishes alongside international wines in an upscale setting.

The Half Cookie

The Half Cookie

3 Boylston St ste 3a, Chestnut Hill, MA 02116

Café🍰 Dessert📸 Instagrammable❤️ Local Favorite🥐 Pastries👠 Trendy
Hemlock Grill

Hemlock Grill

1281 W Roxbury Pkwy, Chestnut Hill, MA 02467

🧦 Cozy🍽️ Dinner🍽️ Gourmet❤️ Local Favorite
Far Out Ice Cream

Far Out Ice Cream

1930 Beacon St, Chestnut Hill, MA 02467

🍽️ Casual🍨 Ice Cream Lively❤️ Local Favorite👠 Trendy😊 Welcoming
The Capital Grille

The Capital Grille

250 Boylston St, Chestnut Hill, MA 02467$$$

👗 Chic🍽️ Dinner❤️ Romantic🥩 Steakhouse🍷 Upscale😊 Welcoming

Outpost of the upscale steakhouse chain offers classic American fare & a clubby, refined setting.

Glazed Bytes

Glazed Bytes

199 Boylston St, Chestnut Hill, MA 02467

Café🧦 Cozy📸 Instagrammable🥐 Pastries👠 Trendy

This café offers specialty coffee, croissant waffles, and grilled cheese sandwiches, all house-made and topped with signature sauces.

Chestnut Hill Restaurant

Chestnut Hill Restaurant

616 Hammond St, Chestnut Hill, MA 02467$

💰 Affordable🇺🇸 American🍳 Breakfast🍽️ Casual🥞 Diner🥪 Lunch

Compact, daytime restaurant providing a variety of traditional American eats in an unfussy interior.

Van Leeuwen Ice Cream

Van Leeuwen Ice Cream

55 Boylston St Suite 5578, Chestnut Hill, MA 02467

🍽️ Casual🍰 Dessert🍨 Ice Cream❤️ Local Favorite🏢 Modern👠 Trendy
The Chocolate Bar

The Chocolate Bar

140 Commonwealth Ave, Chestnut Hill, MA 02467

🏡 Charming🧦 Cozy🍰 Dessert📸 Instagrammable🥐 Pastries

Sweet tooth heaven offering decadent, handcrafted chocolate treats, delightful pastries, and rich hot cocoa. Cozy atmosphere perfect for dessert lovers and casual dates. A must-visit for chocoholics.

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