What to See, Eat & Celebrate This Fall in Greater Boston

What are the best upcoming fall events and new restaurants to explore around Brookline and Boston this season? From festive street fairs to buzzworthy restaurant openings, here's your seasonal guide to what's happening in and around Brookline, Newton, and Boston.

🎉 Upcoming Fall Events You Shouldn't Miss

Newton Highlights

• Newton Harvest Fair (Oct 19) — A community staple with live music, artisan vendors, food trucks, and pumpkin activities on Newton Centre Green. Great for all ages.

Boston Fall Events

• Head of the Charles Regatta (Oct 18–19) — A massive rowing event on the Charles River with festive energy, food vendors, and beautiful views.
• Boston Halloween Events (late Oct) — The city turns spooky with themed tours, costume parties, and kid-friendly parades.

More Ways to Celebrate Fall

• Visit local farms and corn mazes just outside the city for hayrides, cider donuts, and photo-worthy moments.
• Check community centers and libraries for low-key Brookline events like nature walks, craft nights, and farmers markets.

🍽️ Brookline & Boston New Restaurants to Try This Fall

Brookline New Restaurants

• Iru (238 Washington St, Brookline Village) — A refined Korean dining experience serving modern dishes in an intimate setting. Dinner only.
• ZA'TAR Mediterranean Cuisine — A new kosher spot offering flavorful, plant-forward Mediterranean meals. Great for vegetarians and adventurous eaters alike.
• Brookline Lunch — A second location of the Cambridge favorite is opening soon at 1046 Beacon Street. Expect hearty, comfort-style dishes with local flair.
• Bar Vlaha — Recently featured in Eater Boston’s "38 Essential Restaurants," this Greek newcomer highlights rustic, regional fare with warmth and style.

Boston Restaurant Openings Worth the Trip

• Fallow Kin (Cambridge) — One of Boston Magazine’s most anticipated 2025 openings, Fallow Kin blends seasonal ingredients with high-concept creativity.
• The Block at Woods Hill — Part of a growing eco-conscious dining movement, The Block offers upscale experiences with sustainable sourcing.
• Hot list picks include Mimi's Chūka Diner, Little Sage, and Black Ruby—all bringing something distinct to Boston’s food scene this season.

🌿 Why Fall Is the Perfect Time to Explore

Fall in Greater Boston brings cooler temps, stunning foliage, and a surge in both events and dining options. Whether you're a longtime local or a newcomer, this season gives you a front-row seat to what makes neighborhoods like Brookline and Newton feel alive and connected.

From discovering a cozy wine bar to dancing to jazz in Newton Centre, fall is full of opportunities to plug into the rhythm of the community. And with so many new restaurants opening, your next favorite meal might be closer than you think.

✅ Final Takeaway

There’s no better season to explore your neighborhood than fall. With new flavors, lively events, and so much to see and do, Brookline and Boston are bursting with reasons to get out and enjoy. Highlighting these experiences isn’t just good content—it's great community connection.