There’s no shortage of great places to wine and dine in and around New England. Whatever your flavor, whatever your preference or your cravings – we’re sure to have something made just right and just for you in and around the region. New Orleans-inspired Cajun food? Over-the-top ice cream sundaes and milkshakes? 1AM pizza by the slice or all the steak and seafood you can eat in a sitting? Yeah, we’ve got it all.
So with this coming Sunday being the first “official” day of Summer (and Father’s Day! Shout out to all the great dads out there!), I thought I would take some time to rank/count down some of my favorite seasonal spots in New England to grab a quick bite to eat during the hot and humid days we all desperately fight through the Winter to get to!
The places on this list are primarily based around different parts of Massachusetts, with one quick getaway to New Hampshire included, and they’re all places I’ve mentioned/written about here on ‘Coffee & Chiffon‘ in the past – so you might already be familiar with them – but nearly all are locations that are only open during the Summertime, so you have to get there while you can!
But for anyone visiting, be it to check out our coastal aesthetic during this time of year, while passing through a road trip, or for any FIFA-related travels – these are all worth stopping by!
5. Howard’s Drive-In (West Brookfield, MA.)
I had highlighted Howard’s in a “Local Loves” installment last year, and for very good reason. This roadside food stand, which has been in operation since 1947, serves up insane portions of fried seafood, sides, burgers, hot dogs and ice cream – all at a reasonable price and all with a fun, old-fashioned-Summer vibe while you either wait for your food or enjoy it on-site, complete with classic rock and beloved MoTown music playing over speakers around the property.
My favorite thing to order? The fish and chips – although I like to swap out the fries with tater tots, instead. The cut of haddock is gigantic and fried to perfection!
4. Hot Dog Annie’s (Leicester, MA.)
Similarly, I had written about this little hot dog shack for the first time at the height of the pandemic in 2020, although my family and I had been coming here each and every Summer since I was a little kid (and when my parents were little kids before that!) This place is a New England staple for anyone who enjoys the quintessential Summertime cookout food and it has also been in operation since the 1940s – so they know how to cook them up and slather them in the toppings of your choice fast and expertly!
My favorite thing to order? “The Works”! A hot dog covered in relish, mustard and diced onion – with a side of chips, of course!
3. Local Burgy (Haydenville, MA.)
I’m a big fan of Local Burger in Northampton, Massachusetts, but I’m an even bigger fan of the food truck they opened further down the road in Haydenville a few years ago since that location serves up insanely good BBQ, lobster rolls, Captain Crunch chicken tenders (which is exactly what it sounds like!) and some of the best macaroni & cheese I’ve ever had in my life. With plenty of outdoor seating, this is perfect to visit when you’re with a group of friends/family to have a great lunch or dinner together.
My favorite thing to order? The pulled pork sandwich with a side of buffalo and bleu cheese-loaded fries!
2. Kooks (Rye, NH)
With the amount of times I’ve written about Kooks over the years, beginning back in 2020 when it was still just a beachside take-out stand, it wouldn’t surprise me if people thought that it would have claimed my number one spot on this list. I love everything about this place – from their location, to their super chill surfer aesthetic to their incredible staff and the unique, inclusive events they have throughout the season – but their food and beverage selection is also amazing and is worth the drive to experience for locals and non-locals alike. It isn’t Summer until I’ve visited Kooks, and I’ve already been a few times this year!
My favorite thing to order? The street corn chicken tacos and the chips with elote dip. For a beverage? You can’t beat their “Banana Hammock” mocktail!
1. The Bistro Box (Great Barrington, MA.)
And finally, when it comes to both flavors and presentation, you can’t beat The Bistro Box out in the Berkshires. Their food and ever-evolving menu and specials make Summer in New England the tastiest season by far. They also have a great, spacious outdoor seating area with plenty of shade and outdoor games for families – so be sure to bring your loved ones and your appetites because I can promise you – you’re not ready for the absolutely staggering portions!
My favorite thing to order? The “Box Burger” – smothered in bacon jam – and their parmesan truffle fries! Also, if they have their blueberry or raspberry lemonade available, get two! Trust me!
** BONUS ** Cindy’s Drive-In (Granby, MA)
While my list is limited to five snack stops, it didn’t feel right to not include Cindy’s, which is about as retro a roadside stop as they come. While this place serves up some great, greasy food like fries and burgers that are made with both nostalgia and a lot of love – it’s their expansive ice cream selection that makes it a destination worth traveling to. They have, literally, over 100 flavors to choose from – all of which can be turned into a milkshake if you’re looking for a mess-free sweet treat. And they don’t hold out on the serving size! You get a TON of ice cream!
My favorite thing to order? A thin mint cone or milkshake!
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I might be hitting up one of those stops (or more!) on Sunday to celebrate the start of the season and Father’s Day. My dad loved a good roadside food stand, after all. I think that’s where I get it from!
I hope you all have a wonderful weekend ahead, and if you’d like to share your own favorite Summertime snack stops, around New England or beyond, feel free to reach out or drop a comment! I love checking out new places.
See you all on Monday!
xo
Coffee & Chiffon 
Beals in Maine. Their small is a normal person’s large. Be mindful if ordering.
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