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American, Fast food
Special Diets
Vegetarian Friendly
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meals, features
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Reviewed 3 April 2019 via mobile

Just happened to be walking around the City Dock area of downtown Annapolis when I literally stumbled across this magnificent establishment. Very friendly staff and owner. Restaurant named after his daughter. Will definitely visit again! When in Annapolis you must visit this authentic old time...Annapolis Eatery.More

Date of visit: April 2019
Reviewed 13 March 2019

Don't count of a seated fine dining experience. This is a place for a quick dog/hungar fix. Sit on a stool at the window looking at Ego Alley (named for the show-offs running their boats into the City harbour) and chomp down on a fine...Dog. Several selections. All pretty good. Fix 'em up as you like. Get some fries and a soda. A specialty shop. Simple. Small. Clean. Friendly. Priced right.More

Date of visit: March 2019
Reviewed 20 January 2019 via mobile

We both had the Chicago dog. Spot on taste wise with excellent ingredients. Only thing holding it back back from five stars is the dog is skinny. A little bigger dog would nail it. Very tasty dog, though. The staff is very friendly and quick....It is tight inside.More

Date of visit: January 2019
Reviewed 28 August 2018

A place in the central square where the best hotdogs south of Nathan's can be had. Usually crowded, understandably because of the good hot dogs

Date of visit: August 2018
Reviewed 20 August 2018

So so hot dogs, cramped carry out place. Great location need a better tasting dog like Nathans or Sabrett

Date of visit: September 2017
Reviewed 16 July 2018 via mobile

Love stopping in at Pip’s when in downtown Annapolis (DTA). Hot dog creations are amazing and cheesesteaks are the best around! Hot, fresh and delish!

Date of visit: July 2018
Reviewed 11 July 2018

It's difficult to screw up a hot dog, let's face it. This place delivered on every hot dog we tried: plain, Corn Dog, NY and Almost Chicago. Everyone enjoyed the flavor of theirs and the fries were perfect. The price is steep but they have...to pay rent, right? Walked in with our own drinks and walked out with 2 baskets of fries and 3 speciality dogs for $21.00 give-or-take. It was a nice break from a sit down restaurant or fast food; our entire family enjoyed it.More

Date of visit: July 2018
Reviewed 16 October 2017

I ate here 3 straight days during the Annapolis powerboat show. I cannot wait to go back for lunch ASAP. I tried and fell in love with the "Brunch Burger" the first day and had it twice during my 3 visits. The guy working the...grill (I think his name is Paulie) works his rear end off! They have a system worked out and everything is freshly cooked to order and once it's ready to come off he asks "what's going on the ---" and you tell him what you want. Unless you order from the menu then it's topped as advertised. Not a big menu but what they have is super fresh, high quality and cooked perfectly! I suggest buying a "Standby dog" for those less fortunate. Highly recommend this place!! You will not be disappointed.More

Date of visit: October 2017
Reviewed 9 October 2017 via mobile

Ate here 4 straight days during the Annapolis Boat Show. Great dogs, sausages and cheesesteaks. High quality meats, fresh ingredients, fast, friendly service and low prices! You can tell that these guys really care about turning out a great product.

Date of visit: October 2017
Reviewed 16 September 2017

For a little hole in the wall place, if you can eat anything, my husband said best cheese steak in town. I have to eat gluten free, and had an all beef hotdog on a plate. Did a slamming business near the Naval Accemedy.

Date of visit: September 2017
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Frequently Asked Questions about Pip's Dock Street Dogs

Yes, Pip's Dock Street Dogs offers takeaway services.

Yes, Pip's Dock Street Dogs offers delivery services.

Pip's Dock Street Dogs is rated accordingly in the following categories by Tripadvisor travellers:
  • Food: 4.5
  • Service: 4
  • Value: 4
  • Atmosphere: 3.5