Neighborhood Character & History

Brookline exudes a distinctive character with its blend of Victorian and Colonial architecture, wide sidewalks, and an atmosphere that feels both sophisticated and welcoming. Stately brick apartment buildings stand alongside single-family homes with manicured gardens, while commercial districts buzz with activity yet maintain a human scale that encourages walking and exploration. The neighborhood is divided into several village centers—Coolidge Corner, Washington Square, and Brookline Village being the most prominent—each with its own unique personality and offerings.

The area's history dates back to 1705 when it was incorporated as a separate town from Boston, a status it maintains to this day despite being surrounded by the city. Brookline's development was shaped by its proximity to Boston, with wealthy Bostonians building country estates here in the 19th century. The arrival of streetcar lines in the late 1800s transformed Brookline into one of America's first commuter suburbs. This history of independence and careful urban planning has resulted in a community that fiercely protects its character while embracing diversity and innovation—qualities that are deliciously evident in its food scene.

Food & Dining Scene

Brookline's culinary landscape is a vibrant tapestry woven from diverse cultural threads, with particularly strong Jewish, Asian, and Mediterranean influences. The neighborhood offers everything from casual eateries to special occasion destinations, with a refreshing emphasis on independent establishments rather than chains.

At the heart of Coolidge Corner, Zaftigs Delicatessen stands as a beloved institution serving Jewish comfort food that draws crowds for weekend brunch. Their potato latkes, overstuffed sandwiches, and matzo ball soup have achieved legendary status among locals. The restaurant's name—Yiddish for "juicy" or "plump"—perfectly captures its generous portions and hearty approach to dining. Mid-range prices and a casual atmosphere make this an accessible spot for visitors seeking authentic Jewish cuisine.

For an upscale dining experience, La Morra in Brookline Village offers northern Italian cuisine in a romantic setting. Chef Josh Ziskin crafts seasonal menus featuring handmade pastas, wood-grilled meats, and regional Italian specialties. Their tagliatelle with Bolognese sauce and the salt-crusted branzino are standout dishes worth the splurge. The restaurant's warm brick walls and intimate lighting create the perfect backdrop for a special evening out.

Asian cuisine enthusiasts will find paradise at Sichuan Garden II in Washington Square, housed in a historic bank building. Beyond its exceptional Sichuan cuisine featuring numbing-spicy flavors and expertly prepared classics like dan dan noodles and twice-cooked pork, the restaurant harbors a secret: upstairs is The Baldwin Bar, an acclaimed craft cocktail destination. The combination of authentic regional Chinese food at moderate prices with world-class mixology makes this spot unique in Boston's dining landscape.

For a more casual meal, Cutty's in Brookline Village has elevated the sandwich to an art form. This tiny shop creates masterpieces like the Roast Beef 1000 (with sharp cheddar, crispy shallots, and thousand island dressing) and the Saturday-only pork fennel sandwich that inspires lines down the block. Using premium ingredients and house-made condiments, Cutty's represents the best of Brookline's food philosophy: unpretentious yet uncompromising in quality.

Mediterranean flavors shine at Taberna de Haro, where Chef Deborah Hansen's authentic Spanish tapas and extensive sherry selection transport diners to Madrid. The restaurant's outdoor patio becomes one of Brookline's most coveted dining spots in warm weather, perfect for enjoying paella, gambas al ajillo (garlic shrimp), and an impressive selection of Spanish wines. Mid-range prices and a lively atmosphere make this a neighborhood favorite.

Brookline is also home to Gantetsu-Ya, a tiny Japanese spot specializing in takoyaki (octopus-filled dough balls) and okonomiyaki (savory pancakes). This budget-friendly hidden gem offers an authentic taste of Osaka street food that's rare to find outside Japan. The limited seating and focused menu exemplify the specialized, quality-driven approach that characterizes many of Brookline's best eateries.

Beyond restaurants, the Brookline Farmers' Market operates every Thursday from June through November, bringing fresh produce, artisanal cheeses, baked goods, and prepared foods to Coolidge Corner. This weekly gathering has become as much a community event as a shopping opportunity, reflecting Brookline's commitment to supporting local food systems.

Coffee Shops & Bakeries

Brookline's café culture provides the perfect venues for lingering conversations and neighborhood people-watching. Kookoo Café in Brookline Village serves exceptional coffee in a cozy, art-filled space. Their breakfast sandwiches and homemade pastries have developed a devoted following, while the friendly baristas often remember regulars' orders. The café's commitment to quality extends to their carefully sourced beans and house-made syrups.

For those with a sweet tooth, Clear Flour Bread is a destination-worthy bakery specializing in European-style artisanal breads and pastries. Tucked away on a residential street, this neighborhood treasure often sells out of favorites like their pain au chocolat and sticky buns by mid-morning. Their crusty baguettes and rustic loaves are widely considered among the best bread in Greater Boston, making the slight detour from the main commercial areas well worth it.

Tatte Bakery & Café in Coolidge Corner offers a bright, airy space filled with the aroma of freshly baked goods. Founded by self-taught pastry chef Tzurit Or, this local chain has maintained its quality and charm despite its expansion. Their shakshuka, Jerusalem bagel sandwiches, and ornate pastries reflect the founder's Israeli heritage and have made Tatte a beloved breakfast and lunch destination for both locals and visitors.

Shopping & Local Businesses

Brookline's retail landscape favors independent businesses that reflect the neighborhood's sophisticated yet unpretentious character. Brookline Booksmith in Coolidge Corner has been a literary haven since 1961, offering thoughtfully curated selections across genres, frequent author events, and a wonderful used book cellar. The knowledgeable staff provides personalized recommendations that online algorithms simply can't match.

For cooking enthusiasts, Eureka Puzzles offers an impressive selection of brain teasers, games, and puzzles for all ages. This unique shop emphasizes educational value and creative thinking, with staff members always ready to demonstrate products and help customers find the perfect challenge.

Fashion-conscious shoppers appreciate Mint Julep, a women's boutique featuring independent designers and carefully selected clothing and accessories. The shop's curated collection strikes a balance between trendy and timeless, reflecting Brookline's sophisticated style sensibility.

Food lovers shouldn't miss Bazaar on Harvard Street, an international market stocking specialty ingredients from Eastern Europe, Russia, and beyond. From imported chocolates and candies to fresh-baked breads and an impressive selection of smoked fish, this market provides a culinary journey without leaving Brookline.

Cultural Attractions & Green Spaces

Brookline balances urban energy with abundant green spaces that provide respite from city life. The crown jewel is Larz Anderson Park, the town's largest recreation area, featuring rolling hills, an ice skating rink, and the Larz Anderson Auto Museum housed in a former carriage house. The museum displays America's oldest car collection, with vehicles dating back to 1899, while the surrounding 64-acre grounds offer spectacular views of Boston's skyline.

Literary enthusiasts make pilgrimages to JFK National Historic Site, the preserved birthplace and childhood home of President John F. Kennedy. This modest house on Beals Street provides insight into Kennedy family life and the early influences that shaped the future president. Guided tours offer a glimpse into America's most famous political dynasty and their connection to Brookline.

The Coolidge Corner Theatre, a restored Art Deco movie palace from 1933, stands as one of the nation's most successful independent cinemas. Beyond showing a mix of first-run art house films, classics, and cult favorites, the theater hosts director Q&As, film festivals, and special events that have made it a cultural cornerstone of the community.

For outdoor enthusiasts, the Emerald Necklace park system designed by Frederick Law Olmsted includes portions that grace Brookline's borders. Olmsted Park and Riverway offer walking paths, cycling routes, and peaceful spots for contemplation amid thoughtfully designed landscapes that seamlessly blend natural and created beauty.

Nightlife & Entertainment

While Brookline isn't known for wild nightlife, it offers sophisticated evening entertainment options that reflect its community character. The Publick House in Washington Square boasts one of the region's most impressive beer selections, with a particular focus on Belgian brews. The cozy, pub-like atmosphere, complete with a fireplace for winter evenings, makes this a perfect spot to sample rare beers while enjoying elevated comfort food like their renowned mac and cheese.

For cocktail aficionados, Blossom Bar represents the creative reinvention of a longtime Brookline Chinese restaurant (Sichuan Garden) by award-winning mixologist Ran Duan. The tropical-inspired drinks feature house-made ingredients and innovative techniques, while the full menu of authentic Sichuan cuisine makes this much more than just a drinking destination.

Live music enthusiasts gather at The Burren in nearby Davis Square (technically in Somerville but easily accessible from Brookline), an Irish pub featuring traditional sessions and performances ranging from folk to rock in its back room. The authentic atmosphere and quality performances have made this a regional destination for music lovers.

Conclusion

Brookline offers a delicious slice of New England life that balances cosmopolitan sophistication with neighborhood warmth. Its village centers reward unhurried exploration, revealing culinary gems, cultural treasures, and green spaces that locals cherish. For visitors seeking an authentic experience beyond downtown Boston's tourist trails, Brookline provides a perfect day trip or base for exploring the greater Boston area.

Insider tip: Visit on a Thursday to combine the farmers' market with a matinee at the Coolidge Corner Theatre, followed by dinner at one of the neighborhood's outstanding restaurants. And don't overlook the less-trafficked Washington Square area, where some of Brookline's best dining experiences await those willing to venture beyond Coolidge Corner. Whether you're a dedicated food enthusiast, culture seeker, or simply in search of a charming neighborhood to explore, Brookline's distinctive character and diverse offerings create an experience that feels both quintessentially Boston and entirely its own.