Pip's is awesome!! My go-to sandwich here is a Chicken Cheesesteak. Get it with grilled onions, red hots, cooper Sharp white American, lettuce and mayo... you will not be disappointed!!! Also, of course... a standard cheese steak is excellent. They now have Philly long peppers as an option (Anaheim) for cheesesteaks as Pip's stays on top of all the sandwich trends to bring them to you in downtown Annapolis! They have COOPER SHARP! on the menu for my go-to cheese choice. The dogs are great as well, but I just can't overlook a cheesesteak when I hit Pip's. This is an old school order at the counter place where they are shouting the order to the guy on the grill as you're placing it. Service is quick and don't overlook the call ahead ordering option! Sometimes parking downtown is annoying... call in your order. By the time you find a spot and walk to Pip's, your order will be waiting. read more

See all

OMG! This place is amazing. Cool little whole in the wall right behind the Navy Academy and across from where the boats port in downtown Annapolis. Prices were fair and service was great. The hotdog was beef and has a great color and was crisp, hot, was put on a Texas toast type of split bun that was toasted. It was DELICIOUS! The fries were fleshy and you get a bag worth of you order to go. Good size fries (fries boogie here) and the toppings that were so MD was liquid obay sauce "like yes!" . We love hotdogs and having a snap when you bite into it a MUST! Pips is a local joint and did not disappoint. Walking distance to many shops and all the toppings you need. It's a small shop and everything is prepared to order so be prepared to have a little wait. There is some seating outside and a small bar top inside the shop. They also have cheesesteaks and many more items for your pleasure. I will DEF be back and the owners are super hospitality and just nice humans-please please go check them out! "Real testimony"! read more

See all

Having grown up in the area, cheesesteaks are not what Annapolis is known for. Finding a good one, let alone a *great* one, is not easy (especially if you're trying to find that authentic Philly vibe). It had been a while since my last visit to Pips: I had come here a lot in high school and college especially during the summer. My go to was always two hot dogs and a side of fries. But yesterday I was fiending for a cheesesteak and Pips delivered. It was served on a traditional Amoroso roll and I opted for wiz wit as opposed to Cooper sharp or provolone (I get the hype, but I wanted the OG style). For half a sub, it ran me about $8 and I feel like this was a great value for the cost. The steak they use is more of a ribbon versus a finely chopped method, but I didn't mind. It was plentiful, rich, salty, and exactly what the doctor ordered. Would definitely order it again. The cheese fries were pretty standard. That ooey, gooey nacho cheese vibe and the fries were hot and crispy. Solid. And a good amount for what you're paying for. If these fries were hand cut, this would be like out of the ballpark home run level. As far as service goes, it's a family run spot so they do an amazing job. Super polite, positive vibes, very friendly. I think I was in the door and out with my food within about 10 minutes. Regarding vibes on the inside, they've got a wall that celebrates the community, the staff was chatting with the regulars from across the counter, you can see into the food prep area, and they were playing old school hip-hop yesterday. It's the exact type of dive where you'd wanna take your out of town friends when they ask to go to a hidden gem. I will say though that because the space is small, the seating is super limited on the inside (honestly it's just a counter), but they do have patio chairs and tables outside which would be perfect in the summertime. Only note I have is if they opted for a freshly baked crustier roll that had a tad more chew, I think the cheesesteak here would be at Angelo's or Del Rossi levels (iykyk). But as far as cheesesteaks in Annapolis go, Pip's has the sauce. read more

See all

banger dog!!!!! It was quick and exactly what I wanted. It's definitely a place to get food and then walk around to eat it. Will return! read more

Pip's Dock Street Dogs - The Almost Chicago Dog - Hot Dogs Near Me - Annapolis, Maryland

Fun place to grab a yummy hotdog by the water. Not much seating so you might have to walk with it if you're there at a busy time.

My half smoke was delicious. Service was fast and friendly. Nice view of the water, but small. Highly recommend read more

Pip's Dock Street Dogs - Half Smoke! Delicious! - Hot Dogs Near Me - Annapolis, Maryland

If you're looking for a good old-fashioned hot dog with some fixings, this is the spot! It's a small spot, but outside, we got a nice view of the water and boats in the harbor. The hot dog and fries we ordered were solid! From what the guys said, the Coney Island dog is their best seller, and my husband agrees! The workers there were super cool Will definitely be making our way back for another round. read more

See all

My son and I went today for lunch I had a chili dog with french fries it was absolutely delicious the people that work there are very nice my son had the steak and cheese and he said oh yeah ma we going back so yes definitely the food was delicious read more

I'm from Arizona originally, presently in Nebraska. I stopped by Pip's Dock Street Dogs while visiting my really good bro Kon, and I'm so glad I did. The food was absolutely amazing, packed with flavor and clearly made with care. What really stood out, though, was the service. It was top-tier, genuinely welcoming, and made me feel like a local from the moment I walked in. If you're in the area, this spot is a must visit! 10 out of 5 stars! Now every time I visit, it's gotta be mandatory to stop here. read more

See all

The ambiance is a small hot dog diver spot. This is a must visit if you're in Annapolis. The service is always on point.

Really yummy, simple burgers. Cooked great and lots of fun topping choices. They didn't love that I wanted a bun less burger- trust me- I'd rather eat my burger on that bun too but doctor has told me no gluten and I try not to cheat even though I really want to Only two tables and this place is busy. Luckily it was decent weather and we found a spot around the area to sit. Give it a try for sure! read more

The true test of a good dog is a regular beef dog with sauerkrraut & mustard. Pip's is the best! More than a hot dog stand, less than a restaurant. The perfect fast, hot to go treat with a friendly delivery and menu to keep you coming back. (it's a good thing Pips isn't open when the bars close ... they'd need a bigger boat.) read more

OMG I Love this place! Hot dogs are a comfort food for me and they really do it right, lots of great combinations and I really enjoy trying all their different mustards I keep coming back over and over, today I had the grill bratwurst and it was phenomenal. I have to come back to try the cheese steak but every time I come in I end up getting a dog. This is not what you call high cuisine by any means, but if you enjoy a good hot dog then you will enjoy this place. read more

Pip's Dock Street Dogs - Outside view, there are stools inside facing the window and a couple outside tables - Hot Dogs Near Me - Annapolis, Maryland

While I was there today a homeless man came in and got a free hot dog from them, the employee was super nice and welcoming to him. The guys that work there are world class individuals, super nice guys. And the food is so good. Best cheesesteak and dogs in town. Love it read more

Classic, and absolutely amazing. The cozy environment of the spot truly elevates the experience, and that combined with the classic Chicago flavors really makes the experience perfect. read more

Pip's Dock Street Dogs - Hot Dogs Near Me - Annapolis, Maryland

Great hot dog and Cheesesteaks today. We come into town just to eat here. Love this place. Highly recommend!!!

Another downtown Annapolis restaurant that I always saw busy - I HAD to go. Walking down to the pier and passing the establishment constantly, my nose wouldn't let me delay a visit any longer. And truthfully, I should've BEEN a customer. I called my order in before my lunch, was told my wait would be 10 minutes. I walked downtown to the establishment, gave and cashier my name and was paid and back outside within 3 minutes - if that. Great good, great customer service. 5/5! read more

Pip's Dock Street Dogs - Hot Dogs Near Me - Annapolis, Maryland

See all

Good food, friendly staff and quick service. Brunch burger was good, also tried their cheesesteak and American burger during my week there. Very much recommend! read more

Incredibly delicious and a total surprise! Great value as well. We walked in cold and were amazed!

Their food is always great and service is always above and beyond!! The crew always works great together

Great dogs. Great service. I'm a hot dog snob and this place is at the top. The sauerkraut dog was the best.

Nice little stand where were able to quickly get lunch and eat it outdoors in Annapolis while all the other places had long waits and didn't really have any good place to sit outside, but only had enclosed outdoor spaces that might as well be indoors when it comes to air ventilation. The food was good, but not something amazing. I got two hot dogs (the Boyd and a Coney Island), while everyone else hamburgers, fries and chicken tenders. The Boyd wasn't as good as I wanted it to be given that a half smoke is a Maryland thing and it sounded like one of their signature hot dogs. It was just dryer than I wanted it to be. The Coney Island dog was pretty darn tasty though. The chili made it moist in a way that was much better. The chicken tenders and fries came with a spicy and sweet sauce that made me really like it but also meant I had to find the parts that weren't coated in it to feed to my daughter. Live and learn. Next time I'll ask for it only part or on the side. The chicken and breading were really good though. Honestly, I might have gotten them over the hot dogs completely and certainly over the Boyd. The hamburgers looked good, but I didn't try them. My son ate most of his, which is par for the course and my wife said hers was fine, but nothing special. read more

This place is right in the heart of Annapolis. The whole place is mainly taken up by the grill and food prep. There is countertop/bar seating inside and like two tables outside. It is very much quick service place. It is really straight forward. The menu has great variety for how small the place is! We got the LA Street Dog and cheese bay fries. The portions are really big and we shared this amongst two people. The fries were ok... kinda soggy/under fried. The hotdog was really good tho! It was really big and filling. I would definitely come back here when I'm in the area! The cheesesteaks looked really good from what I saw and I will definitely try it next time. Give this a try if you want a snack or quick meal. Prices are really good too for the amount of food you receive and the area! read more

Pip's Dock Street Dogs - Inside - Hot Dogs Near Me - Annapolis, Maryland

See all

Glad for hot dog place with veggie options. Veggie dog is good. Limited seating but the view is great. Service is incredibly fast. Prices are great too. read more

Pip's Dock Street Dogs - Veggie NYC - Hot Dogs Near Me - Annapolis, Maryland

While walking around I noticed the street sign for Philly Cheesesteaks. The restaurant itself needs some work and serious cleaning, but the food made up for a star. They gave you a bag o fries which was awesome m. They had Jones Soda on tap with free refills and that was hands down two more stars. It looks like a family owed business and one tied to the community. With a deep cleaning too to bottom left to right this place would easily be a 5 star. read more

See all

Want a piece of hot dog heaven? Stop by this place for great dogs and great service - everyone was so nice! I had the Boyd (minus American cheese) and the Coney Island. I actually liked the Boyd better. The hot dogs had great snap but the chili could use some salt or something. Altogether they were still good. As forewarned there is limited indoor and outdoor seating but that's okay I wanted to take it back to my hotel room and shamelessly stuff my face! read more

Pip's Dock Street Dogs - The Boyd no American cheese - Hot Dogs Near Me - Annapolis, Maryland

See all

Stopped at Pip's on Sunday, St. Paddy's day. Town was insane with the parade. They announced they were out of corn dogs and fries around 2:30. Handed my wife the 2 1/4 pound dogs we ordered then announced no more 1/4 pounders. Told her they were the last 2!! They were good as usual! There are 2 tables outside if you want to sit and eat your dogs. read more

Best dogs in annapolis by far , 2nd in Md!' The gate pound dog is my favorite , local spot that deserves all the review read more

Omg!!!!! Major Key Alert: Every Wednesday, if you order a cheesesteak, you get a free drink and chips! This is a steal. They're cheesesteaks are phenomenal. Also, you won't find a better dog in town. How do I like my cheesesteaks??? With a hotdog on the side read more

Pip's Dock Street Dogs - Hot Dogs Near Me - Annapolis, Maryland

Great food! Love the natural sausage with none of the extra junk! Great food and staff!

Unfortunately I did not take any photos of the food I got from Pip's but it was nothing less of amazing! We ordered the old bay fries which were amazing and so much flavor! We ordered a Coney Island which is there number one seller, we came back for seconds!! It was so good! We ordered their classic cheese steak as well as their Pip's Burger! The cheese steak was delicious and the burger was very flavorful and juicy! read more

Pip's Dock Street Dogs - Hot Dogs Near Me - Annapolis, Maryland

Delicious dogs of so many variations, scrumptious fries, and the best freshly made hamburgers in Annapolis! The guys are friendly, quick, and always have a pleasant word. No none sense, real good food! read more

Great quick bite to eat if you're feeling a hot dog. They have all sorts of variations of hot dogs, burgers, cheesesteaks, and fries. The corn dogs are also popular. I got the tijuana and it was delicious. The dogs come out pretty quickly and you can watch them cook everything. Beware, if you order fries, they're HUGE-definitely more than enough to share. The service was also good. The employees are very kind and welcoming. My only complaint is that there is very limited seating inside (4 stools facing the window) although there are 2 small tables outside. There also wasn't any AC inside and it was a hot day so I was sweating while eating. Overall I thought the experience was very good and I would come back! read more

See all

A cute little shop that's sits about three people that you can tell it's been open a while. Steady crowd coming through the four. The hit dogs are large, well-cooked, and delicious. read more

Food was wonderful and really hit the spot. Fast and friendly service. Would definitely stop here again.

Great, tiny, casual spot with solid hot dogs and burgers by the docks. Friendly counter service, reasonable prices. I was here with my wife and young daughter; my daughter never eats that much, so I got a burger and fries and my daughter got a hot dog and chips, and my wife said she would just eat whatever of the hot dog my daughter didn't eat. The fries were $4.something, but it was enough for 2-3 people. Everybody liked the food, I would definitely go back. read more

Pip's is a family-run hot dog joint located off of Dock in downtown Annapolis. Using Sabrett dogs, they offer all beef, Polish, spicy, corn dogs, turkey dogs, veggie sausage, and hot Italian sausage, in addition to burgers, cheesesteaks, and sides. I ordered the 'Almost Chicago' Dog (swapped out the all beef with a spicy version; came with mustard, neon green relish, diced onions, a pickle spear, two slices of tomato, sport peppers, and a sprinkling of celery salt; this was just okay, and while I missed the poppy-seeded bun, I think I should have stuck with a regular all beef!), and the Coney Island Dog (all beef dog with homemade chili, diced onions, and mustard (which I left off); the dog itself was super tasty - slightly salty and thin; the chili itself was forgettable, as it was a little watered down). I think I'd probably get just a simple all-beef dog next time, a create-your-own, and/or try out the Pip's Dog, the Tijuana, and the Italian sausage. Staff are very friendly! The place is a tight squeeze; it has has a small counter, but it's mostly to-go; there are some tables outside to chow down. Parking is a little scarce, and there can be quite a bit of congestion from the traffic circle. +all beef dogs +friendly staff +some tables outside +limited parking read more

See all

I am obsessed with hotdogs as the best singular meal in the sense that if you customize it enough, it's the perfect size meal. Now, I was convinced I found the best hotdog at five guys. Little did I know pips was there to absolutely steal the show. Not only was the customer service friendly as it gets, but the hotdog I got (the Boyd) was a brilliant creation comprised of chipotle mayo, sweet peppers, BACON, onions, and of course- the dog itself. I HIGHLY recommend this place for everyone in the whole world. If you want something that hits the spot like nobody's business, this is your place. read more

Pip's Dock Street Dogs - The Boyd - Hot Dogs Near Me - Annapolis, Maryland

I love a good Coney Island Dog, and haven't had one in yearssss... so decided to give this place a try after a day of shopping in Annapolis. They are super friendly, I was greeted with a warm welcome, they were not very busy so, when I said I wanted a Coney Island, the two guys behind the counter jumped right on it. Within 30 seconds I was ready to go! It was exactly what I wanted, the snap of the hot dog was great, and the chili was delicious. And around $5 it is a perfect snack. read more

This place made me make a list of places I like to eat, in my phone saved their hotdogs were amazing. Their cheesesteaks were great and their chicken tenders were surprisingly good. read more