Explore Boston's Downtown Crossing Shopping District

You'll find far more to do than shop in this pedestrian-friendly area near the Freedom Trail and Orpheum Theatre.

Love—or need—to shop? Boston's Downtown Crossing shopping district provides plenty of options in a pedestrian-friendly environment. But history and theater lovers will find much to see and do near the district. Enjoy!


A must-visit, Brattle Book Shop (est. 1825) is three floors—plus, in good weather, a parking lot—full of used, rare and antiquarian titles. European discount retailer Primark’s 77,000-square-foot space offers plenty of excuses to shop. If slow fashion and quality menswear is more your style, head to Clothing From Italy.


Several sites on The Freedom Trail are near Downtown Crossing, including Old South Meeting House, King’s Chapel, Park Street Church and Granary Burying Ground, go at it on your own or take a guided tour. Live performances in a historic setting are at Orpheum Theatre, featuring Steely Dan, Il Divo and “Sleeping Beauty Dreams.”


For a hearty, flavorful lunch, Chilean spot Chacarero is sure to deliver. The namesake sandwich consists of chicken, beef or both,  Mast’ is known for authentic Italian dishes and superb Neapolitan wood-fired pizzas. Serving outstanding drinks and wide-ranging fare, hip supper club Yvonne’s has added exclusivity to the mix with The Gallery—the entrance to the seven-table space is behind a bookshelf. 


Start your day strong at Ogawa Coffee. This Japanese café, which made its international debut in DTX, consistently serves terrific brews alongside a variety of sandwiches and salads. For a healthy sip or pick-me-up, Thirst Juice Co.’s vegan, gluten-free and, most importantly, delicious green juices or smoothies are the way to go, or warm up with a hearty soup. The natural wines at the cozy Haley.Henry, coupled with charcuterie or discerningly sourced tinned fish, make for a great way to wind down.