Boston neighborhood Digital Guide

Recommendations from Off The Beaten Path Food Tours including our Official Tasting Spots. Trust us, they're worth a visit.

View Guide By Neighborhood:
+ Fenway
+ Jamaica Plain
+ Roslindale

Fenway, Boston

Two polaroids showing a mural at Fenway Park and the famous Citgo sign. 

Boston, Massachusetts is the capital of Massachusetts: it is home to over 700,000 in a state of 7 million people. The population density is high and only growing, and one area that has exploded in the 2000’s is the Fenway neighborhood. Part of the Emerald Necklace park system, Fenway is only about 1.25 square miles but is home to many area college students from Boston University to Simmons.

The name “Fenway” comes from the word “fens” which is a British term for low, marshy area. When the area marshland was filled in under the direction of Frederick Law Olmsted who also designed New York’s Central Park, the area was divided in multiple sub-neighborhoods.

The city’s famous Citgo sign sits over by Commonwealth Avenue in Kenmore Square. Nearby, Fenway Park was opened the same year the Titanic sunk in 1912. As you wander the streets down Brookline Avenue, you’ll see Fenway Green, the color of the park and nearby streets. Today Fenway is thriving, with not only new buildings in development but also plans for a huge indoor arts center and one-acre park.

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Neighborhoods Cafe(96 Peterborough Street, Fenway)Created by a neighbor who lamented the fact that there wasn’t a coffee shop in the neighborhood, this place is the real deal and much beloved by area residents.

What to order

Any of their incredible crepes, we love the tuscan chicken and sweet simplicity Their coffee is can’t-miss, too!

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Tasty Burger (1301 Boylston Street, Fenway)As the Official Burger of the Boston Red Sox, this place has serious street cred. Visit the Fenway location just steps from the Park, and you’ll know what we mean. Sink your teeth into a tasty burger and lots of yummy sides.

What to order

We love their tater tots and milkshakes​ too!


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Eventide Oyster Co. (1321 Boylston Street, Fenway)Portland, Maine is a favorite among locals for a long weekend or foodie day trip. Luckily, a bit of the Portland magic came to Boston with this hidden gem, and there’s lots to discover on their menu from oysters to seasonal flavors.

What to order

So many delicious options on the menu and the top oysters in the city; we love their brown butter soft serve​.
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Blackbird Doughnuts (20 Kilmarnock Street, Fenway)These folks put the “art” into artisanal donuts. With quirky flavors and a rich taste, the Fenway neighborhood embraced these sweets with open arms

What to order

Any of their yummy, buttery ​donuts.


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Neighborhoods Cafe (96 Peterborough Street, Fenway)Created by a neighbor who lamented the fact that there wasn’t a coffee shop in the neighborhood, this place is the real deal and much beloved by area residents.

What to order

Any of their incredible crepes, we love the tuscan chicken and sweet simplicity Their coffee is can’t-miss, too!

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Citizen Oyster House (1310 Boylston Street, Fenway)This friendly local hang-out has incredibly high quality eats, from a whole hog roast to oysters to yummy burgers to a fun outdoor patio. Come on in!

What to order

Try their yummy oysters or delicious ​hamburger.


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Time Out Market BostonOpening in May 2019, this marketplace is a local attraction.

What to order

Explore local cuisine from casual to high-end at this unique marketplace, which also has 2 bars.

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Bleacher Bar (82A Landsdowne Street, Fenway)It’s such a treat to visit Bleacher Bar, especially if you’re a fan of baseball. With a view of historic Fenway Park, Bleacher Bar serves up delicious eats to fans and guests alike.

What to order

Any of their subs, sliders, or chili hits the spot!


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Craft Beer Cellar (98 Van Ness Street, Fenway)You’d be hard pressed to find a place with more knowledgeable staff. This place is a true wonder for craft beer aficionados and novices alike. The entire store is brimming with creative energy and exciting limited edition finds.

What to order

Ask the staff for help choosing something to suit your palette.

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Ramler Park (130 Peterborough Street, Fenway)An oasis in the city, this park was created in collaboration with the Ramler family who were prominent and generous business owners and also the City of Boston under Mayor Menino.​

What to order

Relax and smell the roses.

Jamaica Plain, Boston

Two polaroids showing Jamaica Pond and a platter full of chocolates.  

Jamaica Plain, Boston, MA is known as “JP” to the locals. It’s a known secret that JP has some of the tastiest and freshest food in Boston, but it’s a bit hidden from the “beaten path” destinations such as nearby Fenway Park. In fact, some JP residents want to keep it that way, and this tight-knit community is definitely keen on preserving its neighborly feel.

 A small city, JP is only 4.4 square miles and has 40,000 inhabitants. Today’s population of JP is extremely diverse, with many college students moving into its apartments starting in the 1990’s, and also one of the city’s largest hispanic populations of over 30% which is reflected in a lot of its food.

The early inhabitants of JP were well-to-do farmers supplying vegetables and fruits to Boston and also home to the country estates of government officials, professional and literary men, and city merchants. Many Bostonians summered here. There’s two large pieces of land in JP that were designed by Frederick Law Olmsted (1822-1903) who also designed Central Park in NY and is widely considered the founder of landscape architecture.

On one side of town is the world-famous Arnold Arboretum that is 281 acres of land and has thousands of trees, and the other is Franklin Park (first called West Roxbury Park), which is a large 527 acre natural park. That’s why Jamaica Plain was once described as the “Eden of America.” Up near Centre Street where we are now is Jamaica Pond.

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City Feed & Supply (672 Centre Street, Jamaica Plain and 66A Boylston Street, Jamaica Plain)City Feed & Supply gets its name from the rural backgrounds of owners Kristine and David, neither of whom had grocery experience before opening the store in 2008. In their local feed stores, they remember neighbors congregating over a coffee – an experience they wanted to replicate here in Boston.

What to order

Their nitro coffee and kombucha on tap​ are made by worker-owned companies that support small farmers. They also offer a great selection of delicious treats and quality beverages. Wander their store to research local brands you may have never discovered.


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Espresso Yourself (767 Centre Street, Jamaica Plain)This recently opened cafe in a former gallery space is owned by first-time entrepreneur Feruz. It’s a friendly, modern cafe right across the street from the famous Loring-Greenough house.

What to order

They import fresh halvah from SumSum in Amsterdam, who makes the sesame seed confectionery abroad. Espresso Yourself also serves delicious stuffed savory pastries and other pastries from local suppliers.


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Blue Frog Bakery (3 Green Street, Jamaica Plain)This tiny, dog-friendly spot is owned by Chef Brad Brown and won Boston Magazine’s Best Bread recently.

What to order

On Saturdays they serve their famous chocolate almond croissant bread pudding​ and delicious pizzas are often available on Fridays.


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Carrot Flower(703 Centre Street, Jamaica Plain)Named after owner Audrey’s favorite song, this homegrown local cafe offers the most delicious healthy smoothies, salads, and bites.

What to order

We love everything on the menu including the smoothies and cacao treats.


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Fiore’s Bakery (55 South Street, Jamaica Plain)This cafe features vegan, vegetarian, and gluten-free cuisine and is a verified JP establishment!

What to order

Sit out on their patio and try a delicious peanut butter boomerang.
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Cafe Beirut (654 Centre Street, Jamaica Plain)From the outside, a local diner may not know that Cafe Beirut has such fresh and interesting Lebanese dishes inside. Co-Owner Sami Saba’s father started one of the first falafel chains in Boston. Beyond falafel, this inventive stops serves a variety of mezze, including many vegetarian options, and we cannot stop talking about it.

What to order

Try their labneh which is made from a 100-year-old recipe, and bastorma meat which is cured as a cross between corned beef and pastrami.


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Chilacates (658 Centre Street, Jamaica Plain)
Named after a type of Mexican chili pepper, this popular Mexican street food stop was created in 2015 by JP resident Socrates Abreu who still lives in the same JP home he grew up in.

What to order

we adore their tacos which are made from the recipes of Socrates’ Mexican sister-in-law. Chilacates marinates its meats for hours, and they are so flavorful it’s worth all the effort.

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Fomu (617 Centre Street, Jamaica Plain)Started by a local couple, Fomu is known for its non-dairy ice cream that is made with coconut milk and nut milks such as cashew and almond.

What to order

Their vegan chocolate chip cookie is rated as the top cookie in all of Boston by Instagram blogger @chocolatechipboston, and we agree!


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JP Licks (659 Centre Street, Jamaica Plain)In the heart of Centre Street, this regionally-famous ice cream cafe was named for its first location. Started in 1981, the current location is its third move and was home to a former fire house. A kosher establishment, JP Licks is known for its crazy ice cream flavors.

What to order

One of their 300+ ice cream flavors including crazy ones like cucumber, noodle kugel, or disco inferno (Tabasco).

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Blue Nile (389 Centre Street, Jamaica Plain)Although a little bit of a walk from the Centre Street City Center, we love this Ethiopian restaurant for its fresh, unique food that tastes very authentic. You can eat with your hands here, and scoop up meat with injera bread.

What to order

Try a sampler of their veggie dishes with a meat, which is served on top of injera bread.

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Turtle Swamp Brewery (3377 Washington Street, Jamaica Plain)Yes, we know that Sam Adams is the most famous brewery in JP. Turtle Swamp is a local favorite and the self-pronounced “beer of Jamaica Plain.” In fact, Turtle Swamp was the colonial name for the swamp that used to be a filter for waters that became crystal clear and were used for making beer. In fact, there used to be 24 breweries in JP at the start of the 20th Century.

What to order

We love their All Ears golden ale that is made entirely with ingredients from Massachusetts, but there are a variety of beers on tap.

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Taylor House Bed & Breakfast
(50 Burroughs Street, Jamaica Plain)
Ever wanted to stay inside a 1853 Italianate Victorian mansion? Add some amazing artwork and really delicious breakfast, and you’re in luck. Co-owner Daryl also manages a catering company so you’re definitely in good hands in this historical B&B.

What to order

Look for availability on their website next time you or your guests are staying in town. They also own a catering company that provides fresh, seasonal meals for your event.


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Loring-Greenough House (12 South Street, Jamaica Plain)A well-preserved, mid-Georgian is the last surviving 18th century residence in Sumner Hill, a historic section of Jamaica Plain, Massachusetts, the Loring Greenough House is listed on the National Register of Historic Places and is designated both a Massachusetts Landmark and a Boston Landmark.

What to order

Take a free tour of the House on Sundays between 1-3pm (suggested donation $5). They also host fun events such as a weekly summer event called Thursdays on the Lawn which attracts hundreds and also has food trucks and a farmstand.

Roslindale, Boston

Two polaroids showing Tony's Market and a cafe in Roslindale. 

Located in the City of Boston, Roslindale used to be covered by Roxbury which also included the area which is now Jamaica Plain and West Roxbury. Roslindale way back in 1630 when it was part of Roxbury was primarily used for farming at the time, and it wasn’t until the 1840’s that the residents started to work towards separating the towns.

Originally it was called “South Street Crossing” because of the name of its railroad station at South Street which is now where the Roslindale Village MBTA stop is. Roslindale was renamed after the town of Roslin in Scotland which also had similar geography including hills and valleys. It was named by John Pierce who said it reminded him of Roslin. He himself was born in England. He incorporated the use of the word “dale” which means open valley, which is in reference to the south where we have the Blue Hills. As Roslindale developed, so did its architecture and they built not only impressive large Victorian and Queen Anne homes but also smaller bungalows and 2 and 3 family houses. Today the town itself has around 34,000 residents currently and is rapidly growing and thriving.

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Square Root (2 Corinth St, Roslindale)This multi-use cafe quickly became a central meeting spot for Rozzie residents, and there’s even evening concerts.

What to order

A delicious homemade chai or local coffee which uses beans roasted in Massachusetts.


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Fornax(27 Corinth St, Roslindale)This homegrown bakery has a from scratch baking program including its famous sourdough and other delights including scones, soups, and homemade sandwiches.

What to order

You can’t go wrong with some sliced bread and baked goods.


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Blue Star Diner(11 Corinth St, Roslindale)This greek breakfast joint is known for its omelettes, and there’s quite the selection.

What to order

A delicious omelette plate.
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Las Palmas(4337 Washington Street, Roslindale)A small hole in the wall, the staff here are friendly and excited about Latin American casual eats.

What to order

A delicious empanada which isn’t greasy at all!


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Romanos(4249 Washington Street, Roslindale) Although this place has changed hands over the year, they serve a mix of Mexican and Italian cheap eats.

What to order

We are big fans of their Sicilian pizza slices.


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Effie’s(37 Poplar St., Roslindale) This fast casual greek counter restaurant may be tiny but serves up delicious family-friendly fare.

What to order

We enjoy their spanikopita, souvlaki, and large gyros bursting with flavor.


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Shanti(4197 Washington Street, Roslindale) The best indian food in town, this location is quite popular with local Roslindale residents including their lunch buffet.

What to order

Shanti does the standards really well from tikka masala to korma.
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Square Root (2 Corinth St., Roslindale)This multi-use cafe quickly became a central meeting spot for Rozzie residents, and there’s even evening concerts.

What to order

We love the homemade gelato and sorbet.


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Jimmie’s Cafe(48 Corinth St., Roslindale)Local is the name of the game here as they serve only Puritan Ice Cream which is made right in Roslindale since the early 1900’s.

What to order

They have a unique cheesecake ice cream and a rotating list of flavors
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Sofia’s Grotto (22 Birch St, Roslindale)We love how they use meat from local Tony’s Market, this spot has a romantic feel and cute patio for a date night.

What to order

Their artichoke hearts, arancini, meatballs, and pasta entrees hit the spot.


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Delfino(754 South St., Roslindale)Another great Italian gem, this spot tends to get busy and has delicious offerings from seafood to ravioli.

What to order

Order your favorite Italian food here and definitely enjoy the bread.
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Turtle Swamp Brewery(4228 Washington St., Roslindale)We visit here on our Jamaica Plain Boston Food Tour, and this Roslindale Village outpost is inside the historic Roslindale Substation



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Distraction Brewing(2 Belgrade Ave., Roslindale)The newest brewery in town, the team behind Distraction waited for over a year to open this new hot spot.

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Tony’s Market (4381 Washington St., Roslindale)At the helm of this local gem is Tony, who grew up in Italy during WWII and loves opera. He puts his personal touch on the market, and together with his partner Deb and their manager Sue, they sure know food! What to order: any of their high quality meats, cannoli



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Roslindale Main Street(4236 Washington St., Roslindale) Purveyors of the famous Saturday Farmers Market, this organization is the heart and soul of the Roslindale business district. Stop in to say hello!

Boston Affiliate Discounts With Food Tour Purchase

City Feed & Supply (672 Centre Street, Jamaica Plain):Show your food tour ticket confirmation email to receive a 10% discount on all purchases excluding wine and beer.

Neighbors Offer Discounts Too:

Red Apple Farm at the Boston Public Market (100 Hanover Street, Boston):Mention Off The Beaten Path Food Tours to receive 10% off any item including their famous apple cider donuts.

​​​Taza Chocolate Tours (561 Windsor Street, Somerville): invites you to their “Intro to Stone Ground Chocolate” tour with $3 off the tour ticket using the code “BEATPATH” at check-out so ticket prices will now be $5 each. Enjoy!

​​​​Gracie’s Ice Cream (22 Union Square, Somerville):Mention food tour for a free upgrade to Fluff cone with the purchase of ice cream

​​​​Q’s Nuts (349 Highland Ave., Somerville):​Show food tour tickets confirmation email to receive 10% off any purchase within six months of the food tour date; valid at Somerville store only.

​​​​Opa Greek Yeeros (378 Highland Ave., Somerville):Show same-day food tour tickets confirmation email to receive 20% off any purchase that day.

​​​​Bloc Cafe (11 Bow Street, Somerville):Mention food tour to receive a free coffee with the purchase of a bag of Intelligentsia coffee.

Fenway neighborhood discounts:

Cambridge School of Culinary Arts (2020 Mass. Ave., Cambridge) Invites you to ignite your culinary passion and use the special code OFFPATH15 for 15% off any single-day cooking class.

Neighbors Offer Discounts Too:

Acupuncture Together (2464 Mass. Ave., Cambridge) Invites you to show your food tour ticket confirmation email for $5 off your first or follow-up treatment within seven days of the food tour ($30 first visit (regularly $35-55) or $15 follow-up (regularly $20-40).

​​Camberville Dog Treats (561 Windsor Street, Somerville)Invites you to use code “cdttour” for 15% off all natural dog treats made in Camberville on their website.

​​Rhode Island Red Food Tours Invite you to try a food tour of Newport or Providence, RI and use code “RIMAFOODIES” for 10% off the booking fee. We’ve been on their food tours, and they’re wonderful too!