One Massachusetts deli lists a sandwich called Disheveled Brisket. The same menu offers Unkept Tuna Salad and Sloppy Hot Roast Beef, which sounds less like a warning and more like a promise.
Honestly, I love when a sandwich shop admits it can’t keep things neat. Messy names usually mean the kitchen isn’t shy with the fillings.
Another stop on this list sells a sandwich called the Pastrami Diablo, and I’m already curious how spicy that gets.
I love how a great sandwich can turn an ordinary lunch stop into the highlight of your day. Whether it comes from a busy city counter, an old-school Italian market, or a little shop in a quiet town, there’s something irresistible about a sandwich that’s almost too big to pick up.
And honestly, if you need both hands, a mountain of napkins, and a little determination to finish lunch, I’d say you’re off to a good start. The only question is whether you’re saving half for later or convincing yourself you can finish the whole thing.
1. Michael’s Deli
Any menu that names a sandwich Disheveled Brisket is clearly not trying to impress the neatness police. Sloppy Hot Roast Beef and Unkept Tuna Salad sit right beside it, and you can guess how tidy those turn out.
This longtime Brookline spot is a family-owned Jewish deli in the classic New York style. Overstuffed sandwiches are the main event, though bagels and other old-school deli dishes hold their own.
Corned beef is a big draw here. It’s the kind of sandwich that reminds you why delis became famous in the first place.
Bagel fans have plenty to cheer about too. The lox and cream cheese bagel comes loaded with sliced tomato, onions, and lettuce, and the portions are generous.
Don’t skip the knishes. The housemade version is vegan, and it has the comforting, grandma-style feel people hope for from a knish.
Potato latkes are another smart add-on. You can order a set of four cocktail latkes, which makes a great side for sharing or not sharing.
Want the full throwback? Grab a Dr. Brown’s root beer and maybe a half order of chopped liver if you’re feeling bold.
Ordering happens at the counter, and you’ll find seating inside plus some outdoor seating. It works well for a solo lunch or a quick bite with a friend.
Timing matters, so plan ahead. Monday hours run only until 2 PM, while Tuesday through Saturday stretch to 4 PM and Sunday closes at 3 PM.
Parking on Harvard Street can be tricky, so give yourself a few extra minutes. Reservations aren’t taken, which keeps things simple and casual.
Brookline has plenty of lunch choices, but few feel this rooted in deli tradition. Bring your stretchiest pants and a real appetite.
Address: 256 Harvard St, Brookline, MA 02446
2. Sam LaGrassa’s
Blink and you might miss lunch here, since the doors open only from 11 AM to 2 PM on weekdays. That tiny window hasn’t stopped this family-run downtown Boston shop from earning serious praise.
Specialty sandwiches built on traditional deli meats are the whole story. The sizes are massive, and one sandwich is more than enough for most people.
Pastrami gets star treatment on this menu. The Pastrami Traveler and the fiery-sounding Pastrami Diablo both show how far a classic can stretch.
Can’t pick between two favorite meats? The Pastrami and Corned Beef Combo solves that problem in one very full sandwich.
A classic Reuben is here too. So is a Cuban sandwich, which is a fun change if you want something pressed and hearty.
The Spicy Chicken Cutlet and the Southwest Pastrami also bring big flavor. Sides like coleslaw help balance things out, and it happens to be vegan.
Service is fast and friendly, which matters when half of downtown seems to want lunch at once. There’s usually a wait, so arrive with a little patience.
Ordering is done at the counter, and you can eat in or take your sandwich to go. Curbside pickup and delivery are options if you can’t break away from your desk.
Street parking nearby is paid and often hard to find. Walking or taking the T is the stress-free move in this part of Boston.
Weekend visitors will need to adjust plans, because Saturdays and Sundays are closed. Put it on a weekday itinerary and you’ll be glad you did.
Bring a friend or bring a container. Either way, this lunch might turn into dinner too.
Address: 44 Province St, Boston, MA 02108
3. Figaro’s Boston
Fair warning comes up a lot when people talk about these sandwiches. They’re enormous, and that’s exactly why this small Beach Street spot belongs on the list.
Family-run and proudly Italian, the deli turns out elevated sandwiches, wraps, and soups. It’s a hole-in-the-wall kind of place where the food does the talking.
The Italian sub is the one to know. It comes stacked with top-quality cold cuts, hot peppers, onions, lettuce, and just the right seasoning.
Bread matters here, and it shows. Fresh, sturdy rolls hold up to the heavy fillings without falling apart in your hands.
Not in a sub mood? The Chicken Caesar Wrap and Chicken Pesto offer lighter-feeling options that still won’t leave you hungry.
Vegetarian and vegan eaters get real choices too. The shop offers full vegan and vegetarian menus, which isn’t common at an old-school Italian deli.
Keep an eye out for the free brownie on the menu. A sweet bonus after a giant sandwich feels like a little gift from the kitchen.
Hours are short, so plan carefully. Lunch runs from 11:30 AM to 2 PM on weekdays, and weekends are closed.
Expect a wait during the lunch rush. There’s no restroom, so taking your food to go is often the easiest plan.
Delivery is available if you work nearby and can’t step out. Catering is offered too, which could make you the office hero.
Small space, big flavor, and sandwiches that could double as dinner. Your appetite should show up ready to work.
Address: 105 Beach St, Boston, MA 02111
4. Monica’s Mercato
One sub, two people, zero complaints. Sandwiches at this North End market are so huge that splitting one is a very reasonable idea.
Monica’s Mercato is part grocery store and part deli. Shelves hold a wide range of Italian goods, while the counter handles sandwiches, meats, cheeses, and bread.
That combo makes it a fun stop even if you came only for lunch. You can grab a sub and leave with a bag of pantry treats too.
The sandwiches are the headline, though. They’re massive, and the value impresses people who expect smaller portions in a busy tourist neighborhood.
Salem Street sits right in the heart of Boston’s North End. It’s a great area to wander after you eat, especially if you need to walk off a giant sub.
Hours are generous compared to some delis on this list. The doors open from 9:30 AM to 8 PM, seven days a week.
Crowds peak on Friday afternoons and Sunday evenings. Weekday mornings tend to be quieter if you’d rather skip the line.
There’s no restroom, so plan accordingly. Most visits here are quick, which suits grab-and-go eaters.
Bakery items are part of the mix as well. A little something sweet might sneak into your order before you reach the register.
Delivery and in-store pickup are options if you want to order ahead. Parking nearby is paid, and the neighborhood streets are famously tight.
Hungry friends, take note. Bring a buddy, grab one sub, and see who finishes their half first.
Address: 130 Salem St, Boston, MA 02113
5. Regatta Deli
In Worcester, the word grinder gets tossed around with real respect. This family-owned Lake Avenue standby has spent years giving that word plenty of weight.
Regatta Deli is known as an iconic neighborhood spot. Hot and cold Italian grinders lead the menu, and they’re hearty enough to fuel a full afternoon.
Steak and cheese is a top pick. Portions are enormous and fresh, and the prices stay reasonable for the amount of food you get.
The menu is huge, so take a minute before ordering. A wide selection means you can come back often and still try something new.
The famous Regatta sub carries the shop’s name for a reason. It’s the obvious choice for a first visit if you can’t decide.
Save room if you can. Homemade sides and desserts round out the menu, and they add a personal touch to a quick meal.
Plan to take your food to go. There’s no dine-in seating, which makes a picnic by nearby Lake Quinsigamond a tempting idea.
Early birds will appreciate the hours. Doors open at 7 AM Monday through Saturday and close at 4 PM, with Sundays off.
Free street parking keeps the stop easy. Weekday mornings and afternoons stay busy, so a little patience goes a long way.
There’s no delivery, so you’ll need to swing by yourself. Honestly, that’s half the fun of a classic neighborhood deli.
Big grinders, homemade extras, and a lakeside setting nearby. Central Massachusetts lunch doesn’t get much better.
Address: 28 Lake Ave, Worcester, MA 01604
6. Tom’s International Deli
Shaved kielbasa layered into a sandwich is a move you don’t see every day. At this Polish deli on Millbury Street, it’s one of the reasons people keep coming back.
Tom’s International Deli serves signature sandwiches alongside traditional Polish specialties. It brings a different flavor to the Worcester sandwich scene.
Fresh bread and quality cold cuts form the base. Portions are big and consistent, so you won’t walk away wishing you’d ordered more.
The Reuben earns serious praise here. It’s often called one of the freshest around, which is high praise for such a classic sandwich.
Pastrami is another menu highlight. If you lean Italian, the Italian Cold Cut Sub Sandwich is waiting too.
The staff are friendly and attentive. They build sandwiches with care, and that attention shows in the final product.
Shopping is part of the experience as well. In-store shopping means you can browse while your order comes together.
Hours start early on weekdays, from 8 AM to 4 PM. Saturdays run shorter, closing at 2:30 PM, and Sundays are closed.
Monday and Tuesday afternoons get busy, as do Wednesdays. Arriving in the morning could save you some waiting.
Both free and paid street parking are available nearby. Delivery and takeout are options when you can’t stick around.
Millbury Street has a strong Polish heritage, and this deli fits right in. Bring curiosity and maybe a cooler for extras.
Address: 52 Millbury St, Worcester, MA 01610
7. Bob’s Italian Foods
Part butcher, part deli, part Italian pantry, this Medford market wears a lot of hats. Somehow it still finds time to build jumbo subs.
Bob’s Italian Foods has an old-school feel and a very efficient setup. You’ll find Italian provisions, hearty sandwiches, and a full catering operation.
The sub lineup covers hot and cold choices. An Italian deluxe with caprese and a chicken cutlet with meatball both show up on fan lists.
Chicken cutlet parm deserves its own spotlight. It’s huge, tasty, and exactly what you want on a chilly New England day.
Want a classic? The House Italian Deli Combo comes in a small size, which might be the polite choice for lighter appetites.
Beyond sandwiches, the market offers pizza, lasagna, meatballs, and eggplant parm. Fresh bread and pasta make it easy to plan dinner too.
The staff know their stuff. They’re quick to help you find items in the well-stocked case and on the shelves.
Hours are long for a deli. Weekdays run 9 AM to 7:45 PM, Saturdays start at 8 AM, and Sundays close at 2:45 PM.
Free street parking makes stopping easier. Visits tend to be quick, though weekend afternoons can get busy.
There’s no restroom, so take that into account. Delivery and takeout are both available.
Leave room in your fridge before you go. You’ll likely bring home more than one meal.
Address: 324 Main St, Medford, MA 02155
8. Anthony’s Italian Specialties
No frills, no fuss, just jumbo subs that could anchor a small boat. This Stoneham counter keeps things simple and lets the sandwiches do the bragging.
Anthony’s Italian Specialties is known for big Italian-style submarine sandwiches. Fresh bread and generous deli meat are the foundation of that reputation.
The Italian sub is the classic order. It’s loaded with meat and quality ingredients, so one is often plenty.
Meatball subs and chicken parm also hold strong spots. Steak bombs join the lineup for anyone craving something hot and hearty.
Here’s a surprise for an Italian deli. Friday brings a special treat: Anthony’s offers its famous lobster sandwich or sub, packed with lobster meat.
Pastrami rounds out the highlights. It’s nice to have a deli classic mixed in with the Italian favorites.
Ordering happens at the counter, and takeout is the way to go. There’s no delivery, and there’s no restroom.
Breakfast is part of the menu too. Doors open at 8 AM Tuesday through Saturday, so an early start is possible.
Watch the schedule, though. Mondays and Sundays are closed, and Saturday wraps up at 3 PM.
Parking is a breeze, with plenty of free street spots. Afternoons on weekdays get busy, so mornings may move faster.
The vibe stays casual and kid friendly. Reservations aren’t a thing here, so just show up hungry.
Address: 408 Main St, Stoneham, MA 02180
9. Pajer Superette
Superette sounds small, but the grinders coming out of this Agawam deli are anything but tiny. Massive and amazing tend to show up in the same sentence here.
Pajer Superette is an Italian grocery and deli in western Massachusetts. Signature grinders and specialty prepared foods are what bring people through the door.
Portions are huge, and the ingredients are super fresh. That combination makes it a favorite for anyone who wants real value.
Grinder is the local word for a sub in this part of the state. Order one here and you’ll understand why the name sticks.
Prepared foods add another reason to stop. You can pick up something ready to eat later, which saves you from cooking.
The schedule takes a little planning. Mondays and Tuesdays are closed, so don’t make the trip on those days.
Wednesday through Saturday, hours run 8:30 AM to 6 PM. Sunday mornings may offer a quieter visit, but remember that the shop closes at 2 PM that day.
On-site parking makes stopping easy. That’s a real perk compared to the crowded city spots on this list.
There’s no delivery and no restroom. Plan for a quick visit and take your grinder home or to a nearby park.
Western Massachusetts doesn’t always get the sandwich spotlight. This stop makes a strong case that it should.
Address: 400 Cooper St, Agawam, MA 01001
10. Pickle Haus Deli And More
Turkey and corned beef on the same bulkie roll sounds like a delicious argument. The #3 at this Northborough shop settles it with coleslaw, Swiss, and Russian dressing.
Pickle Haus Deli and More is a family-owned sandwich shop with a busy, friendly feel. It’s known for not skimping on the meat, which is the whole point of this list.
The #3 also brings lettuce and tomato into the mix. It’s a towering combo that could make a Reuben jealous.
Classic cold cuts like corned beef, pastrami, and turkey anchor the menu. Wraps add another option if you prefer something easier to hold.
Soup lovers, take note. Homemade soups and chili are part of the lineup, and they pair nicely with a sandwich.
Scones show up too. That’s a fun twist for a deli and a good excuse to grab something for later.
Healthy options and a full vegetarian menu make it easy to bring a mixed group. Coffee is available for anyone needing a boost.
Portions are generous, and prices stay reasonable. Ordering happens at the counter, and dine-in is an option.
Parking is easy here. A free lot and free street parking usually leave plenty of space.
Hours run 8 AM to 3 PM, Monday through Saturday. Sundays are closed, so plan your craving accordingly.
Kids are welcome, and there’s a restroom on site. Delivery is available, including no-contact drop-offs.
Address: 276 W Main St, Northborough, MA 01532
11. Mansfield Deli
A plain building can hide a serious sandwich habit. This Pratt Street deli keeps the outside simple and saves the drama for what’s between the bread.
Mansfield Deli serves fresh breakfast and lunch sandwiches. They’re generously portioned, packed with flavor, and made with quality ingredients.
Early risers win big here. Weekday hours start at 6 AM, so a breakfast sandwich before work is totally doable.
Bagels are on the menu for morning cravings. Lunch brings options like the Roasted Turkey Bacon Avocado and a Cuban sandwich.
Reuben fans have a spot too. Eggplant parm offers a meatless choice that still feels hearty.
Gluten-free options are available as well. That makes it easier to bring along friends with different needs.
Save a little room for sides. The macaroni salad gets a lot of love, and the sides are reasonably priced.
The range of cold cuts is wide. You can build something classic or go for one of the more unique combos.
Weekday hours generally extend into the early evening, although the deli’s published closing times differ between sources. Weekends run from 7 AM to 3 PM, which works for a lazy Saturday lunch.
Parking options include a free lot and free street spots. Busy stretches hit most mornings and afternoons, while evenings tend to be calmer.
Service is friendly and fast. Delivery and takeout are both easy options.
Ending a Massachusetts deli road trip here feels right. Big sandwiches, early hours, and macaroni salad worth bragging about.
Address: 72 Pratt St, Mansfield, MA 02048
Share this story
