Boston specific recommendations from Off The Beaten Path Food Tours including our Official Tasting Spots. Trust us, they’re worth a visit.

Beacon Hill and Downtown Boston

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.

Another important neighborhood in Boston is Beacon Hill, one of the most photographed neighborhoods in Boston. Park Street is a central MBTA stop that is right next to the Omni Parker House, one of the city’s oldest hotels.

The Boston Common and Boston State House building are a stone’s throw away. Established in 1634, the Boston Common is the oldest public park in all of America. Did you know when it first opened it was a cattle grazing ground? There are also many famous paintings of the Boston Common. If you walk further, you’ll reach the Boston Public Market which opened in 2015 and is a year-round indoor public market right next to the North End and alongside the Freedom Trail.

  • A Sanctuary Cafe

    80 Charles Street, Boston Beacon Hill

    Their mission is paramount, both supporting community causes and community cats, and this female-owned neighborhood locale is available for delicious local treats and drinks as well as cat cafe reservations with one of the resident felines.

    What to Order

    We love their MEM tea, rich hot chocolate, and delicious pastries including mini croissants and desserts from French Press.

  • Beacon Hill Books and Cafe

    71 Charles Street, Boston, Beacon Hill

    Afternoon tea and lunch, hidden passageways and delightful bookshelves, you cannot miss this quaint cafe just steps from the Make Way For Ducklings statues. Get ready to explore!

    What to Order

    We love their yummy quiche, coffee, and afternoon tea of course!

  • 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​.

  • 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.

  • Omni Parker House

    60 School Street, Boston

    One of the oldest hotels in Boston, the Parker restaurant is where JFK proposed as well as where the Boston Cream Pie originated along with the famous Parker rolls.

    What to Order

    Explore their yummy menu and don’t forget to finish it off with a slice of Boston Cream Pie (which they can make with or without nuts.)

  • 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!

  • Cheers

    84 Beacon Street, Boston

    You’d be hard pressed to find another place where everyone knows your name! Just a stone’s throw from the Boston Common, this famous bar will bring back nostalgia.

    What to Order

    Typical bar food – go for the ambience!

  • 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.

  • Beacon Hill Chocolates

    71 Charles Street, Boston, Beacon Hill

    Owner Paula has a knack for finding interesting truffles and gifts, and she also sells handpainted boxes in which to store these yummy treasures.

    What to Order

    We love their signature Beacon Hill Chocolates truffle as well as locally sourced bars like from Goodnow Farms.

  • Flour – Boston Common

    Boston Common

    Steps from the Embrace statue, this new Flour location was a long time men’s restroom that was converted into a sandwich shop until it closed and now reopened in 2025.

    What to Order

    Try their delicious soft serve ice cream dipped in chocolate which is new for this location as well as a Flour hot dog! And of course their sticky buns which are always hot out of the oven here.

  • Parlott Chocolatier

    Boston Public Market

    Owner Lucilene has a passion for chocolate and her truffles are absolutely some of the best in Boston.

    What to Order

    We love her passionfruit truffle, white chocolate bars, and cacao.

  • Petrova Chocolate

    61 Salem Street, Boston, MA

    Owner Betty is quite skilled at everything from detailed design to the design of her stores!

    What to Order

    We highly recommend their bon bons which have startling flavors as well as their selection of bars!

Jamaica Plain, Boston

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.

  • City Feed & Supply

    672 Centre 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.

  • Jadu

    767 Centre Street, Jamaica Plain

    This recently opened cafe in a former gallery space is owned by first-time entrepreneur. It’s a friendly, modern cafe right across the street from the famous Loring-Greenough house.

    What to Order

    They have all kinds of yummy toasts, light tea and coffee items.

  • 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.

  • The Joint

    654 Centre Street, Jamaica Plain

    From the outside, a local diner may not know that The Joint has such fresh and interesting dishes. They serve breakfast and lunch.

    What to Order

    Try their yummy breakfast burritos or pancakes.

  • 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.

  • 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.

  • The Haven

    3377 Washington Street, Jamaica Plain

    Yes, we know that Sam Adams is the most famous brewery in JP. In fact, there used to be 24 breweries in JP at the start of the 20th Century. The Haven is a popular Scottish pub here.

    What to Order

    Burger, oatcake, scottish eggs

  • Footlight Club

    50 Burroughs Street, Jamaica Plain

    America’s oldest community theater is in JP. Established in 1877, they have non-professional shows running year-round of all genres.

    What to Order

    Look for availability on their website for tickets to a show.

  • Loring-Greenough House

  • 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).

Roslindale, Boston

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.

  • 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. Also the delicious homemade chai or local coffee which uses beans roasted in Massachusetts.

  • 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.

  • 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.

  • 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.

  • 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.

  • 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.

  • 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

  • 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. Also the delicious homemade chai or local coffee which uses beans roasted in Massachusetts.

  • Sweetie’s

    48 Corinth St., Roslindale

    Although Puritan Ice Cream which is made right in Roslindale since the early 1900’s, these folks actually serve mix-ins and was created by two local moms.

    What to Order

    They have delicious fresh fruit mix-ins we recommend.

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