If you’re wandering around City Dock in Annapolis and you’re not stopping at Pip’s Dock Street Dogs, you’re doing it wrong. I love, love, LOVE this place, and their hot dogs are seriously delicious, so consider this your official push to check them out! It’s a tiny hot dog stand right on Dock Street, steps from the water, and it’s been a downtown Annapolis fixture for around 17 years now.
They’re known for their loaded creations (they also do cheesesteaks and burgers), and the toppings game is next level. My standout this time was The Stavvy, a spicy dog that had a great kick to it, and I’d happily go back to work through more of the menu. For a spot this small, it packs a serious punch, and the fact that it’s survived floods and kept feeding this town for almost two decades tells you everything. Here’s what I got.
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What Makes Pip’s Dock Street Dogs a Must Visit
What makes Pip’s special is that it takes something simple, a hot dog, and treats it like it deserves real care. They use natural-casing all-beef Sabrett dogs and Hebrew National kosher dogs, then let you go wild at a toppings bar that runs from sweet peppers to red hots, plus their own house-made Pip’s Relish and something like 20 different mustards. It’s right on the water at City Dock, so it doubles as one of the most scenic quick bites in Annapolis. This isn’t a gas-station dog situation, it’s a spot that’s been perfecting loaded dogs since 2006, and that longevity in a tourist-heavy, flood-prone stretch of downtown is no accident. When a hot dog stand lasts 17 years on the harbor, the dogs are worth your time.
What to Order at Pip’s Dock Street Dogs
Here’s what I got this time around, and all pricing includes tax, which is a nice touch.
The Stavvy ($8.55)
This was my favorite of the bunch. It’s a spicy dog piled with sharp white cheddar, homemade chili, chipotle mayo, fried onions and hots, and it was fantastic. The hot dog had a great kick to it, and all those flavors worked really well together instead of fighting each other. If you like spicy, this is the one to get, no question.
The Reuben Dog
This was a special they had running, and I’m so glad I grabbed it. It’s a beef dog loaded with sauerkraut and thousand island dressing, and what’s not to love there. The sausage was nice and juicy, and they piled on a TON of sauerkraut, which is exactly what you want. Specials rotate, so if you spot this one, jump on it!
Coney Island ($6.25)
This is their number one seller, and it’s supposed to come topped with mustard, homemade chili and diced onions. Full transparency, mine came out plain by mistake, so I dressed it up at home with ketchup, onions and relish, lol. I didn’t have time to go back, but I can already tell the real deal is a must, and it’s next on my list. At $6.25 it’s a total steal, and there’s a reason it outsells everything else.
A few others worth knowing: their cheesesteaks come on toasted Amoroso rolls (the real Philly move), the burgers are fresh Angus, and the Chicago Dog gets a lot of love from regulars. If you’re plant-based, they even do Field Roast and Tofurky dogs on vegan buns, so nobody’s left out.
A 17-Year City Dock Institution
Part of why I root for Pip’s so hard is the story behind it. It started as a hot dog cart back in 2006, and the owner named it after his daughter’s nickname, Pip. Almost two decades later, they’re still on Dock Street, even after some of the worst flooding Annapolis has seen, which hit them hard in 2024. They bounced back with community and neighbor support, and you can feel that in the place. There’s even a wall where you can pre-pay a meal to donate to someone who needs it. That’s the kind of small business I want to send you guys to.
The Vibe and Experience
Pip’s is small, and I mean small. There are only a few stools and a couple of tables inside with a window view toward Ego Alley, so it’s really more of a walk-up and carryout spot. When the weather’s nice, though, grabbing your dog and posting up outside by the water is the move. It’s casual, quick and friendly, perfect for a lunch break, a stroll around downtown, or a stop before you keep exploring Annapolis. Just know it’s a hop in, order, hop out kind of place, not a sit-down situation.
Good to Know
- Location: 📍 118 Dock St, Annapolis, MD 21401, right on City Dock
- Hours: Tue to Fri 11am to 4pm, Sat and Sun 11am to 5pm, closed Monday
- Price: budget-friendly, and all prices include tax (dogs run about $6 to $9)
- Toppings: a big complimentary toppings bar, from sweet peppers to red hots, plus house-made Pip’s Relish and 20-plus mustards
- Seating: just a few seats inside; it’s mostly walk-up and carryout, with easy outdoor seating by the water in nice weather
- Vegan options: Field Roast and Tofurky dogs on vegan buns
- Also on the menu: cheesesteaks on Amoroso rolls and fresh Angus burgers
- Parking: the metered City Dock lot is closest; Gott’s Court Garage is a short walk, and there’s a free downtown Circulator bus
Is Pip’s Dock Street Dogs Worth A Trip?
Yes, one hundred percent. If you’re anywhere near downtown Annapolis, this is a must-stop, whether you’re a local or just in town for the day. The dogs are yum, the toppings let you build exactly what you want, and the waterfront setting makes a quick lunch feel like an event. This place has my whole heart, and I already know I’m going back for a properly dressed Coney. Pair it with a morning bite at Bread and Butter Kitchen and you’ve got a whole Annapolis food day.
Have you guys been to Pip’s yet? Let me know your go-to dog and toppings combo in the comments, Nomsters! And if you’re making a downtown day of it, Chick and Ruth’s is another Annapolis classic worth a stop. Save this one for your next trip to City Dock.