I recently returned from a little getaway in Boston. Early October is like stepping into a postcard of classic New England charm. The city comes alive with the crisp air of fall, leaves swirling down tree-lined streets, and a sense of cozy sophistication that makes autumn in Boston truly unforgettable. It's the perfect time of year—cool enough for a light jacket, with the warmth of the sun still lingering through the afternoons. The city’s historic beauty is on full display, especially in Beacon Hill, where every corner feels like a step back in time.

Beacon Hill, is one of Boston’s most iconic and picturesque neighborhoods, and is a must-visit during your stay. Its narrow cobblestone streets wind between rows of brick townhouses, each adorned with lovingly maintained window boxes overflowing with fall blooms and cascading ivy. Gas lanterns flicker as evening settles in, casting a warm glow on the streets below and creating a storybook ambiance. Acorn Street, one of the most photographed streets in America, is tucked right here—a dreamy alley that captures the essence of Boston’s old-world charm.

Another wonderful stop on your Boston itinerary is the Henry Wadsworth Longfellow House in nearby Cambridge. This historic site, once the poet’s home, holds a special place in my heart because it was the backdrop for The Children’s Hour, one of my all-time favorite poems and a cherished book I used to read to my children when they were young. Unfortunately we were unable to visit due to the government shutdown. The home where Longfellow once lived and wrote is a place I want to go back and visit!

The city is wonderfully walkable, with many of its treasures nestled close together. From Beacon Hill, you can easily stroll to the Boston Common and Public Garden, where you’ll find the beloved duck statues inspired by Robert McCloskey’s classic children’s book, Make Way for Ducklings. These charming bronze sculptures of Mrs. Mallard and her ducklings are a delight to visitors of all ages and have become an iconic photo spot. I read this dear book to my children on the regular when they were little. So much so the book started to fall apart.

Of course, no visit to Boston would be complete without enjoying its incredible food scene. All around Beacon Hill and nearby neighborhoods, you'll find cozy cafés, delicious restaurants, and irresistible bakeries. Grab a flaky croissant or a pumpkin-spiced treat from one of the local bakeries on Charles Street, or settle in for dinner at a charming bistro with candlelit tables and a menu full of seasonal favorites. Whether you’re craving Italian, seafood, or something sweet, Boston serves it up with flavor and flair.

Whether you're sipping coffee outside a café, wandering through cobbled streets adorned with fall decor, visiting the ducklings in the Public Garden, or stopping by the home of a beloved poet, a fall escape to Boston offers the perfect balance of city excitement and quiet, scenic beauty. It's a place where history meets heart—and where every moment feels just a little more magical in the crisp October air.

ASHLEY’S FAVORITES