South Boston Food Guide: 10 Must-Eat Restaurants & Street Food Stalls in South Boston

April 14, 2018 Frederic Celentano

South Boston is a densely populated neighborhood of Boston, Massachusetts, located south and east of the Fort Point Channel and abutting Dorchester Bay. South Boston, most popularly known as Southie, was once a predominantly working class Irish Catholic community, but has become increasingly desirable among young professionals and families.
Things to do in South Boston

1. Bistro 1888

221 Main St, South Boston, VA 24592-4625 Reservations, Private Dining, Seating, Waitstaff, Wheelchair Accessible, Serves Alcohol, Full Bar American Dinner SGD 20 - SGD 31 +1 434-572-1888
Excellent
74%
Good
20%
Satisfactory
3%
Poor
2%
Terrible
1%
Overall Ratings

4.5 based on 132 reviews

Bistro 1888

Reviewed By Lee R - Front Royal, Virginia

My Spouse was in South Boston for his 50th High School Class reunion. I differed and made a great decision to dine at Bistro 1888. Fine ambiance, fine service, excellent cuisine! I had the chipolte grilled shrimp as an appetizer which was delightful. Then as an entre' I had the Fried Oyster special and it was JUST THAT, SPECIAL. Beautiful crunch with moist tender oyster inside with sides of country mashed potatoes and saute' green beans. I tried the Sky Valley Saugnon Blanc from New Zealand which matched perfectly for my taste. For dessert I had the fresh pear creme brulee. It is a place for relaxed fine dining.

2. Windmill Farm Bake Shop

2221 Wilborn Ave, South Boston, VA 24592-1629 Takeout, Seating, Wheelchair Accessible American Lunch, Breakfast, Brunch +1 434-572-4444
Excellent
76%
Good
23%
Satisfactory
1%
Poor
0%
Terrible
0%
Overall Ratings

4.5 based on 52 reviews

Windmill Farm Bake Shop

Sandwiches made to order, home made soups, cakes, pies, cookies muffins, doughnuts, all made with love by a Mennonite farm family. Prices are so low you'll be amazed. $3.50 yesterday for a roast beef sandwich on whole wheat with light mayo, tomato, lettuce and a bavarian cream doughnut.

Reviewed By Richard P

For breakfast, I prefer the muffins, since they're far less sweet than the donuts. The lemon poppyseed muffins are awesome. For lunch, the cold sandwiches are great. My favorite is chicken salad. If they'd add two things, it'd be perfect in every respect. First, add a pepper bacon to the meat list. Second, add a toasting option for melted cheese. For lunch, be there at 11:30 to beat the heavy noon traffic.

3. Southern Plenty Cafe

206 Main St, South Boston, VA 24592-4626 Takeout, Seating, Waitstaff, Wheelchair Accessible American, Cafe, Vegetarian Friendly, Vegan Options, Gluten Free Options Lunch, Brunch, Breakfast +1 434-575-7675
Excellent
73%
Good
21%
Satisfactory
5%
Poor
0%
Terrible
1%
Overall Ratings

4.5 based on 55 reviews

Southern Plenty Cafe

Reviewed By Jan B - Farmville

We thought the food was okay but the experience would have been better if first, they would get that table with soap displayed out of the way. Much too tight trying to get to the counter to order. Also no one ever came around offering...MoreThanks for your comments. We will be taking them into consideration as we are revamping the floor plan and ordering at the counter option.

4. Darby's Tavern

3105 River Rd, The Berry Hill Resort & Conference Center, South Boston, VA 24592-6011 Reservations, Takeout, Seating, Waitstaff, Parking Available, Television, Serves Alcohol, Full Bar, Accepts American Express, Accepts Mastercard, Accepts Visa, Free Wifi, Outdoor Seating, Highchairs Available, Wheelchair Accessible American, Bar, Pub Lunch, Dinner SGD 9 - SGD 26 +1 434-517-7031
Excellent
57%
Good
25%
Satisfactory
7%
Poor
6%
Terrible
5%
Overall Ratings

4 based on 78 reviews

Darby's Tavern

Darby's Tavern is located in the former Estate kitchens which date back to 1790. Fireplaces used to prepare meals for the Bruce Family are prominent in every room. The tin tables and antique floors create the perfect atmosphere for casual all day dining and unwinding. Besides the best burgers in South Boston, the menu features Southern and Creole favorites once prepared by Darby, the original Berry Hill cook and namesake of the Tavern. Beverage service includes a full array of wines, spirits, unique beers on tap and an extensive list of craft brews. Darby's Tavern also features a billiard room, wifi jukebox and a private dining room for parties and events. Outdoor courtyard dining available in nice weather.

Reviewed By JPMcGuire - South Carolina

It's been a few years since my first visit and when I returned last night I was pleased to find it is still a fantastic place: atmosphere, decor and food. Staff was polite. I had the Salmon BLT. I chose it because it sounded strange...MoreSo happy to hear! Thank you so much for your comments - looking forward to your next visit :)

5. Mexico Viejo Grill

1020 Bill Tuck Hwy, # 800, South Boston, VA 24592-7136 Takeout, Seating, Waitstaff, Serves Alcohol, Wheelchair Accessible Mexican, Southwestern Lunch, Dinner +1 434-575-1775
Excellent
58%
Good
25%
Satisfactory
10%
Poor
2%
Terrible
5%
Overall Ratings

4.5 based on 40 reviews

Mexico Viejo Grill

Reviewed By Mark G - Goochland, Virginia, United States

Enjoyed one of the best Carne Asada meals I have had recently. Great service, Friendly staff. They make a great Margharita. Good value

6. Ernie's Restaurant

1010 John Randolph Blvd, South Boston, VA 24592-2950 Private Dining, Seating, Waitstaff, Parking Available, Highchairs Available, Wheelchair Accessible, Takeout, Reservations, Buffet American Lunch, Dinner +1 434-572-3423
Excellent
46%
Good
25%
Satisfactory
17%
Poor
6%
Terrible
6%
Overall Ratings

4 based on 93 reviews

Ernie's Restaurant

Reviewed By boogaloo94 - virginia

Stopped in a few months ago for a lunch meal.. Buffet meal was good--especially the spaghetti. Waitress was right nice and attentive. Have liked eating here at times for years--- but the place is getting the creepy look on the outside. It really seriously needs some attention. Overgrown ivy/ bushes all up around and on the building front itself.......tighten up owners!!! It looks gross and uninviting and quite frankly sorta snaky looking w/ so much overgrowth b4 you can get to the front door. A real good clean up job to the outside would make it stand out more and bring in more customers.

7. Mi Carreta Mexican Restaurant

3332 Halifax Rd, South Boston, VA 24592-4842 Takeout, Seating, Waitstaff, Wheelchair Accessible, Serves Alcohol Mexican Lunch, Dinner +1 434-572-3776
Excellent
56%
Good
36%
Satisfactory
4%
Poor
4%
Terrible
0%
Overall Ratings

4.5 based on 25 reviews

Mi Carreta Mexican Restaurant

Reviewed By Caitlin S - Bristol

This place was busy as usual. We've been coming here for a few years every time we visit South Boston. We prefer this restaurant to the other 'Mexican' (I use this term loosely) restaurant on the other side of SoBo - Mexico Viejo.

The margaritas were super strong and the food was delicious. The only drawback was having to wait almost an hour for the food - the serving staff all seemed young, like they were doing it as a part-time job between college, and didn't seem that experienced but they were friendly and trying hard.

As with many restaurants in America, they try to fill you up with free starters, this came in the form of some very moreish tortilla chips with salsa and some bizarre kind of blue-ranch sauce that we couldn't stop eating (MSG anyone?) and they didn't stop refilling.

They were accommodating for our vegan family member and made special vegetable fajitas for her. The rest of the table had other fajita variations and I tried the chicken tacos - it was all really delicious and well priced. As with most 'ethnic' cuisine in this part of the world, the food had definitely been adjusted for the American palate and was heavier - laden with cheese and sour cream. I was, however, pleasantly surprised at the level of spice in some of the sauces that came with the tacos.

Other than the long wait, the smell of cigarettes drifting over from the smoking section, kids kicking the back of our booth all night and the creepy old man a few tables down who kept staring at my sister, it was a great night with strong drinks and good food.

8. Dinis Brothers Pizza & Restaurant

901 Wilborn Ave, South Boston, VA 24592-3127 Takeout, Seating, Waitstaff, Wheelchair Accessible Pizza, Italian Lunch, Dinner +1 434-572-3913
Excellent
45%
Good
45%
Satisfactory
5%
Poor
5%
Terrible
0%
Overall Ratings

4.5 based on 20 reviews

Dinis Brothers Pizza & Restaurant

Reviewed By Blokzijl - Green Valley, Arizona

The place was packed, luckily we were able to get seated quickly. Kathy came across from the other side of the room, to wait on us because she recognized our hosts as frequent visitors. Great service level.

Meal started with a local favorite fried green beans, lightly battered and still slightly crisp in side.Though two of our group ordered the small sized version of the steak sandwich, it was enough and very good. The pizza was more than enough for one person. I enjoyed the gyro sandwich, it was huge, really didn't need to order the Greek Salad though it was refreshing.

Taken back by the lack of cleanliness in the bathroom, not sure when that has been inspected. But then the rest of the restaurant also needed some deep cleaning for dust, cobwebs, etc.

9. O'Sole Mio Italian Eatery

Rt. 58 Riverdale Plaza, South Boston, VA 24592 Takeout, Seating, Wheelchair Accessible, Serves Alcohol Italian, Pizza Lunch, Dinner +1 434-575-1270
Excellent
32%
Good
41%
Satisfactory
21%
Poor
3%
Terrible
3%
Overall Ratings

4 based on 28 reviews

Reviewed By rogerc1234 - Clayton, North Carolina

traveling thru south boston recently, we wanted a good local spot for a late lunch. quick google search id'd this place just as we were about to drive by. quick right turn was a good move. order taken by very pleasant young lady at the counter. ordering, service, food and the setting were excellent for a local italian restaurant. salads were fresh and excellent, but with packaged salad dressing, which was quite satisfactory. thin crust pizza was fresh made, cooked properly and very hot, which pizza just out of the oven should be. an excellent place to take advantage of a local establishment.

10. Mansion

3105 River Rd, Berry Hill Resort, South Boston, VA 24592-6011 Reservations, Seating, Waitstaff, Wheelchair Accessible Dinner, Brunch +1 434-517-7000
Excellent
82%
Good
9%
Satisfactory
9%
Poor
0%
Terrible
0%
Overall Ratings

4.5 based on 11 reviews

Mansion

Reviewed By Dick P - Timberlake, North Carolina

Had the duck, and my wife had the shrimp and grits. Great greek salad. Wonderful fried green tomato appetizer.

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