Here’s how to spend the perfect day in Roxbury

In Boston.com’s Perfect Day series, we’re talking to a local expert in each of Boston’s 23 neighborhoods about how they’d spend their perfect day. See what makes this city so special to your neighbors, and share your perfect day with us at [email protected].

Located in the heart of Boston, Roxbury once encompassed present-day West Roxbury and Jamaica Plain from its founding in 1630. Over time, the formerly sprawling agricultural community transformed into an industrial community, and later a strong, tight-knit Irish community starting in the 19th century. 

Now a thriving and diverse neighborhood home to a variety of cultures from the Caribbean, Africa, Latin America, and Asia, the neighborhood is undergoing a renaissance and looking towards a brighter future, according to Roxbury Main Streets executive director Robert M. George.

“I don’t think that any other neighborhood in the city of Boston has the fusion culture[s],” said George. “We have African culture, Caribbean culture, and Hispanic culture along with Asian culture, which makes quite a dynamic potpourri of different things that you can experience there in the city.”

Moving to Boston and working around the city for over 40 years, George has made Roxbury his home away from home. As the executive director of Roxbury Main Streets, he and his team are dedicated to supporting local businesses and entrepreneurs and showcasing all that Roxbury and its residents have to offer.

“My main goal is to maintain a thriving business district in Roxbury [and] Nubian Square specifically,” George said. “[It is] an eclectic environment, [with] a fun, rich historical culture and food.”

As Roxbury has changed, so have people’s perception of the neighborhood.

“Roxbury has a rather challenging past and challenging history, and individuals tend to overlook and not focus on some of the great things that they can enjoy and appreciate,” he said. “I think people tend not to focus on that, and tend to remember only some of the challenges that neighborhood had by neglect, sometimes deliberate.”

As the executive director of Roxbury Main Streets, calling his work schedule busy is understatement. However, George still finds time to frequent his favorite places that are sure to never disappoint, according to him. 

“Roxbury has a very bright future with a number of developments taking place,” he said. “While we love [and] cherish our history, we have to ensure that we move forward with modern facilities, modern buildings, [and] modern retail spaces.”

With Roxbury Main Streets’ regularly hosted events throughout the holiday season and beyond, you’ll want to explore the neighborhood if it has been on your bucket list. 

Here is how executive director George spends his perfect day in Roxbury. 

Morning | Afternoon | Evening | Map | Share your perfect day

Morning: Start your day at Dudley Cafe

After his commute to Roxbury, George likes to stop and pick up breakfast at Dudley Cafe (15 Warren St.). First opening the Roxbury location in 2015, the locally owned cafe now is approaching a decade of serving the neighborhood.

“I find that they have some of what I refer to as the most delicious and scrumptious variety of muffins in the city of Boston,” he said. “[They also have] excellent croissants as well as muffins and coffee cakes.”

For his top grab-and-go items, George recommends a chocolate croissant or blueberry muffin, and a cappuccino to drink.  

“Things that I really enjoy [are] the atmosphere of meeting folks who are busy and bustling [on the way] to work in the morning there. You’re able to sit and get some work done, things of that nature. That’s a wonderful way to start your day in Nubian Square,” he adds.

For a longer, sit down breakfast, head to Silver Spoon Restaurant (2387 Washington St.). This old school restaurant offers a variety of classic diner-like options for breakfast and brunch. For breakfast, George recommends their build-your-own breakfast sandwiches or a breakfast platter where you can get scrambled eggs and sausage. To wash your breakfast down, George recommends ordering an ice tea. 

After breakfast, take a walk around Nubian Square (247 Washington St.) and pop into local clothing stores like Final Touch With Class Boutique (17 Warren St.) and Mabruuk Fashion (37 Roxbury St.). 

Afternoon: Explore Nubian Square

For a midday fuel up, Roxbury has a variety of spots to satisfy a variety of cravings. For a classic handheld, head to Joe’s Famous Subs and Pizza (140 Dudley St.).

“They’ve been there for decades, and they have an environment where you can [get] any subs that you would like. It’s [a] quick turn around [with] wonderful customer service. They have anything from Italian subs [to the] essential meatball subs.”

Serving traditional Nigerian cuisine, Suya Joint (185 Dudley St.) offers an extensive selection of dishes, including options for people with allergy and dietary restrictions. If you’re looking to escape Boston’s cold winter with traditional island cuisine from Jamaica, try P&R Jamaican Restaurant (208 Dudley St.).

Set in Nubian Square, Frugal Bookstore (57 Warren St., Roxbury) is a great place to browse after lunch, says George. The Black-owned bookstore sells books by BIPOC authors for readers of all ages.

“They have created these enclaves of reading spaces [where you] can actually enjoy reading a good book while you’re there. [They] have large collections of African American books, and again, they work also on creating ambience and environment.”

If you’re more the museum-type, the National Center of Afro-American Artists (300 Walnut St.) has amassed a collection with over 3,000 objects and continues to perform Black Nativity as written by author and activist, Langston Hughes, a 50 year tradition for the museum. 

“This museum … places the constitution of artists of the African diaspora,” he said. “It also shows the richness of the African, the Caribbean and the African American culture.”

To enjoy some time outdoors, head to the Roxbury Heritage State Park, home to the Dillaway-Thomas House (83 Roxbury St.), headquarters of the Continental Army during the Siege of Boston in 1775. This historic landmark and museum exposes Roxbury’s role in the Revolutionary War, George said.

Evening: Dinner and live music

After work, the dinner spots in Roxbury come to life. Whether it be a newer restaurant or long-standing institution, there is plenty to explore in the evening, especially if you have a craving for soul food.

“[These] places are so eclectic, everything you can get is good, so [there] is not one thing I can pick out,” George said about his favorite restaurants.

With its “soulful vibes” and “great comfort food,” Slade’s Bar and Grill (958 Tremont St.) lives up to its tagline, “The Soul of Boston.” Since 1935, Slade’s has served Greater Boston comfort food for just shy of a century. Be sure to check out their events page to enjoy dinner and show.

The music and good vibes don’t stop at Slade’s however. George also recommends adding Darryl’s Corner Bar and Kitchen (604 Columbus Ave.) to your Roxbury itinerary. With live musical performances throughout the week and a mouthwatering, Southern-inspired menu, eating at Darryl’s is a must.

For a “taste of the Caribbean” as stated on their website, Fort Hill Bar and Grill (2805 Washington St.) is another option serving favorites like mofongo and paella. 

“I’ve sent a number of individuals there that have had a great time,” said George about Fort Hill.

“There [are] the eclectic vibes that you get from all of these restaurants in Roxbury. [The] African American, the African vibes, the Afro Caribbean vibes, the Latin American vibes throughout the entire Roxbury community,” he said. “The menus are varied and skillfully put together, and are all flavorful and tasty. It’s the best way to wind down your evening.”

Following dinner, head to the historic community center, Hibernian Hall (184 Dudley St.) for a community event. George recommends visiting for a live theater or musical performance from local talent.

“Roxbury has a deep sense of pride and collaboration. From the Revolutionary War to the Civil Rights Movement, it [is] a meaningful place to explore,” said George. “As you walk through Roxbury there are a number of art murals. Roxbury is bursting with creativity evident in public art,” he adds.

“The murals tell powerful stories of identity, struggles and trial, [and] diversity of experience.”

Ultimately, George firmly believes that Roxbury and Nubian Square offer something for everyone.

See all of Robert M. George’s recommendations below.

What does a perfect day in Boston look like to you?

Nia Harmon

Community Co-op

Nia Harmon is a community co-op for  Boston.com and a journalism student at Emerson College. She is a journalism major with a minor in media studies at Emerson College. She is a native of Dallas, Texas.