Food Trail #4: Hot Dog Trail from Fairfield to Milford, Connecticut

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We’re back with our 4th food trail throughout parts of Connecticut. (Check out our CT food trails: cupcakes, chocolate shops, cookies, crepes, tacos, and bakeries.) This time, we’re checking out some of the top rated hot dog spots from Fairfield to Milford. As always, there are so many great spots and we had to set the limit at ten, so don’t take this as a comprehensive list! Many of these spots are casual restaurants, with very tight parking lots, limited indoor dining, and no public restrooms. While they stay open all year, they mainly have outdoor picnic tables for dining. We’ve noted the spots that have indoor seating and restroom facilities. But we guarantee what they lack in size, they MORE than make up for in friendly staff and really good food!

Hot Dog Trail from Fairfield to Milford:

Rawley’s Drive In in Fairfield has been open since 1947 and is rumored to be a favorite of nearby former local Martha Stewart. We have been going to Rawley’s for years, since our college days at nearby Fairfield University. 
We topped it with NOTHING- we’re a Rawley’s purest and love the buttered bun.
Our favorite side: The crinkle french fries are salty and good!
Other options: Burgers, shakes, chicken sandwiches and tenders, fried clams, shrimp roll, grilled cheese. Rawley’s also offers gluten free hot dog and hamburger buns.
Cost: $3.95 + toppings
Full menu here.
The shop is closed on Sunday, and open from 11am-7pm Monday through Saturday. There is a small indoor dining area.

Reef Shack recently opened in downtown Fairfield, near many shops, restaurants, and within walking distance (although it’s about ¾ of a mile) to the beach. It’s quickly becoming a favorite for locals for its large menu and Coffee Corner (a shop within the Shack) which features homemade baked goods.
We topped it with: ketchup. Full disclosure: Reef Shack only offers hot dogs as part of the Little Reefer kids meal (good value!) 
Our favorite side: Four types of hand cut fries, and create your own bowls (pick your lettuce and add up 24 items and 10 different dressings!)
Other options: People rave about the cheesesteak and BECs (bacon, egg, and cheese). There are many options for sandwiches, seafood platters, and salads. 
Cost: $6.50/ Little Reefers meal
Full menu here.
The shop is open 8am-4pm Sunday through Thursday and 7am-7pm Friday and Saturday. There is a small attached indoor dining room, and restroom facilities are available. 

Super Duper Weenie in Fairfield, which has been featured on the Food Network and other popular television programs., is our of our go to spots. Their Weenie truck (which actually came first in 1992 before the storefront opened in 2000) is quite popular and is available for corporate and private events. 
We topped it with chili- not too spicy, which is just how we like it!
Our favorite side: Fries!
Other options: There are almost a dozen speciality hot dogs, plus hamburgers, chicken nuggets, and sandwiches.
Cost: $3.95 + toppings
Full menu here.
: Open seven days a week from 11am-4pm. There is a very tight parking lot. There is an attached indoor dining space with picnic tables and restroom facilities are available.

Cricket Car Hop in Stratford is in a great location, overlooking Sikorsky Airport. Kids will love watching the planes take off and land, and Long Island Sound and local beaches are less than two miles away. The original restaurant was open from 1949 until 2004, and then reopened in 2017.
We topped it with cheese
Our favorite side: Milkshakes (and they’re huge!)
Other options: The shop offers a variety of burgers, sandwiches, seafood, and five options for a kids meal, very reasonably priced. 
Cost: $3.79/ hot dog; $4.59/ 9” hot dog
Full menu here.
: Open from 10:30am to 7pm Monday through Saturday and closes at 5pm on Sundays. There is a big outdoor patio for dining and a smaller indoor dining room. The restaurant also offers a take out window, so guests don’t have to leave their car, but there’s also a large parking lot if guests do want to dine on site. 

Danny’s Drive In in Stratford is located right off Interstate 95 close to nearby attractions and boating docks, on the banks of the Housatonic River. It’s been open since 1935 and is very popular with locals.
We topped it with coleslaw (LOVED it!)
Our favorite side:  Waffle fries and malts
Other options: There are about a dozen different hot dogs, half a dozen burger and sandwich options, and a few seafood sides (clam strips and cod). 
Cost:  $3.49/hot dog with the works; great special on Monday-Thursday from 3pm-closing: 2 hot dogs with toppings and a fountain soda for $5. 
Full menu here.
: Open everyday from 11am (12pm on Sundays) until 8pm-9pm. Take out only, but there are a few picnic tables out front. Very small parking lot. 

Fryborg in Milford opened in 2011, eight years after the owner traveled to Brussels and became obsessed with Belgium double fried fries. He started with a food truck, selling his version of the fries with over a dozen dipping sauces, and then opened the Milford store front. There are about six ways to top the fries, in addition to the 15+ sauces for the fries, dogs, and burgers. The Fryborg food truck travels throughout Connecticut New York.
We topped it with onion and relish
Our favorite side: We LOVED the french fries and 3 sauces we tried: peso mayo, buffalo ranch, and honey mustard.
Other options: Hamburger, veggie burger, chicken sandwich, sausage specials, a couple of salads, and even a Nutella s’more special!
Cost: $4.23/hot dog
Full menu here.
Open everyday  at 11am and closes at 8pm on Sunday through Thursday and closes at 9pm on Friday and Saturday. There are only two hightops for indoor dining. Parking is on Bridgeport Avenue or in the nearby diner parking lot. 

Mr. Mac’s Canteen in Milford also has a Monroe location, and a food truck that heads all over Connecticut for corporate and private events. Both locations serve up a great breakfast (omelettes looked awesome!), a variety of grill options, and plenty of made to order sandwiches. 
We topped it with relish and onions
Our favorite side: Onion rings, but they also have a ton of options
Other options: Burgers, deli sandwiches, about a dozen fried seafood platters, and plenty of choices for grinders.
Cost: $2.65/ hot dog, $3.45/ hot dog for deluxe toppings
Full menu here
Noteworthy: Open at 7am every day, closes at 4pm on Sunday and 7pm-8pm the rest of the week. Small parking lot in front.  

Jake’s Diggity Dogs in Milford is located in a complex right off the Milford Green, and near the marina, both within walking distance. 
We topped it with mac and cheese, and served on an everything bagel seasoning bun (so good!)
Our favorite side: There’s about 25 different types of hot dogs, so we suggest trying a few combos (and get the onion rings too!)
Other options: Hamburger and veggie burger (and veggie hotdog), and ice cream and Italian ice from local shops
Cost: $2.95/ hot dog, $4-$7 for deluxe dogs
Full menu here.
: Open from 11am-7:30pm Monday through Saturday. Currently, they are open for take out only, but traditionally offer a small indoor dining room.

Goodies Restaurant in Milford opened in 2006 and offers all day breakfast, a wide variety of fried seafood, and hot dogs and burgers for lunch and dinner. Seasonally, Goodie’s also serves at Gulf Beach in Milford. 
We topped it with bacon (all hot dogs come with complimentary bacon)
Our favorite side: Fried dough (served with powdered sugar or marinara sauce)
Other options: There’s a wide variety of wraps and seafood platters, as well as burgers and salads. There’s also 7 kids meal options
Cost: $3.49/hot dog, $4.49/long dog; combo meals include fries and a fountain soda for under $9
Full menu here.
: Open seven days a week from 7am-8pm. Both indoor dining and a few outdoor picnic tables outside; restroom facilities available.

Dogtown in Milford is located on the other side of Milford, closer to West Haven. The shop opened in 2017 and also has a food truck (Chevy step van) that’s available for parties and corporate events.
We topped it with cucumber relish
Our favorite side: Milkshakes (black and white, and peanut butter!) and string onion rings. 
Other options: Burgers, fries, almost a dozen sandwiches options, and 5 kids meal options
Cost: $3.75/hot dog (which includes some toppings) to $5.25 for the max.
Full menu here.
: Winter hours are 11am-4pm seven days a week, no indoor dining, but plenty of outdoor tables and chairs spread out on a patio. No restroom facilities. 

Our sources for “research”: Three of our favorite sources for researching anything Connecticut are (the official state tourism website), (THE resource on all things food related), and (a magazine I have subscribed to for years, full of info on a great variety of topics)

For more fun in Connecticut, check out our top 30 list of things to do and our list of 32 places to eat, and check out our CT food trails: cupcakes, chocolate shops, cookies, crepes, tacos, and bakeries. And follow along on our adventures on Instagram, Twitter, Facebook, and Pinterest.

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  1. I once saw Rawley’s on Food Network, I hear their buttered bun is to die for! Great job as usual, gotta check these out! So glad I found a amazing blogger living near me! Keep up with the good work!

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