Two soft cake rounds, a thick layer of creamy filling, and zero chance of eating one neatly. The whoopie pie is a New England classic, and Massachusetts bakeries keep the tradition going one batch at a time.
Some shops build their whole identity around these handheld treats, while others tuck them into cases next to cannoli, cupcakes, and wedding cakes. You will find classic chocolate, red velvet, peanut butter, oatmeal, and even gluten-free and vegan versions.
This list covers eight bakeries from the North Shore to Cape Cod and out to the Pioneer Valley. Each one earns its spot for a different reason, whether it is a wild flavor lineup, an allergy-friendly kitchen, or a waterfront location.
Grab a napkin, maybe two, and plan your next sweet road trip.
1. Topsfield Bakeshop, Topsfield, MA
Wedding cakes may bring in the big orders, but whoopie pies are the signature at this Topsfield shop on Boston Street. The bakery is known for both, which tells you the decorating skills carry over to the smaller treats too.
The flavor lineup goes well beyond plain chocolate. Funfetti, red velvet, and oatmeal varieties show up here, with soft, rich cake and a filling that keeps the sweetness in balance.
They are also good-looking little desserts. If you are bringing a box to a party, presentation counts.
The case also holds cupcakes, macarons, and tiramisu, and the shop serves espresso drinks plus paninis on fresh focaccia. That makes it an easy breakfast or lunch stop, not just a dessert run.
Plan around the schedule. The bakeshop is closed Monday and Tuesday, open 8 AM to 5 PM Wednesday through Friday, until 4 PM Saturday, and until 2 PM Sunday.
Free lot and street parking keep the visit quick.
2. Chococoa Baking Co. & Cafe, Newburyport, MA
Inside a historic mill building at The Tannery on Water Street, Chococoa has turned the whoopie pie into a full menu category. The cafe bakes a wide variety of flavors in house, so choosing just one takes real effort.
Gluten-free whoopie pies are part of the lineup, which is a big deal for anyone who usually skips this treat. Whoopie pies can even be made to order for events and gifts.
Delivery is offered in Newburyport and beyond, so a box can show up at someone’s door.
The rest of the menu leans cafe-style, with espresso drinks, scones, croissants, and other pastries. Free Wi-Fi and a relaxed setting make it a solid spot to linger.
Hours run 7 AM to 4 PM Monday through Saturday and 8 AM to noon on Sunday. That short Sunday window fills fast, so go early.
3. Whoopie-Doo & Cupcakes too, Sturbridge, MA
With a name like that, you know exactly what the priority is. This scratch bakery on Main Street in Sturbridge puts whoopie pies first and cupcakes a close second.
Peanut butter whoopie pies are a standout, and there is also a version covered in chocolate for anyone who thinks a whoopie pie needs more frosting energy. Gluten-free options are available.
The cupcake side gets creative with flavors like lemon drop and white chocolate raspberry. Cheesecakes, fancier desserts, and fresh bagels round things out.
Here is the useful part for road trippers. Sturbridge sits right off the Mass Pike, and this shop stays open until 8 PM Tuesday through Saturday, which is rare for a bakery.
Sunday hours are noon to 7 PM, and it is closed Monday. Tuesday evening tends to be the quietest time to stop in.
4. Greggory’s Pastry Shop, Hadley, MA
Out in the Pioneer Valley, Greggory’s Pastry Shop has built a following for beautiful custom cakes. The whoopie pies, though, are what keep people talking.
This is a specialized bakery with a focus on artisanal pastries and event cakes. The whoopie pies sit right alongside those showpieces and hold their own.
The raspberry pastry deserves a mention too. It has a crisp shell, a soft center, and plenty of raspberry flavor.
I would save this stop for a weekday trip through Hadley, since the shop is open 8 AM to 5 PM Tuesday through Friday and 8 AM to 4 PM Saturday. It is closed Sunday and Monday, and it does not deliver.
Saturday morning is usually the calmest time. There is a free parking lot on Russell Street, which makes grabbing a box easy.
5. Cupcake Charlie’s, Plymouth, MA
Few bakeries on this list come with a harbor view. Cupcake Charlie’s sits on Town Wharf in Plymouth, right where visitors wander between the waterfront and the historic downtown.
Cupcakes are the headline, with fun flavors like cotton candy and hostess. Moist whoopie pies share the spotlight and make a tidy treat for walking the wharf.
There is also premium soft-serve ice cream, so the shop works as a summer cool-down stop. Coffee is available too.
Gluten-free cupcakes are on the menu for anyone avoiding wheat.
The hours are friendly for evening strolls. Doors open at 11 AM daily and stay open until 8 PM Monday through Thursday, 9 PM Friday and Saturday, and 7 PM Sunday.
Prices land in the budget range. Parking nearby includes both free and paid lots.
6. Scapicchio’s Bakery, South Yarmouth, MA
An Italian bakery might seem like an odd place to hunt for a New England classic. On Cape Cod, Scapicchio’s proves the two traditions get along just fine.
This family-owned shop on Route 28 is known for cannoli filled fresh throughout the day, with crisp shells and creamy ricotta. Lobster tails, ricotta pie, cookies, breads, and Sicilian pizza fill out the menu.
The whoopie pies are a favorite here as well, often mentioned in the same breath as the ricotta pie and birthday cakes.
Morning visitors can also grab cranberry or blueberry muffins with a coffee. That makes it a smart stop before a beach day.
Timing matters. Scapicchio’s is open only Tuesday through Saturday from 8 AM to 3 PM, so plan around those hours.
A free lot sits right on site.
7. The Whoo(pie) Wagon, Beverly, MA
Clever names deserve clever treats, and The Whoo(pie) Wagon delivers on the pun. The shop is a dedicated whoopie pie bakery, now open in a new spot at Cummings Center in Beverly.
Red velvet is a popular pick. The lineup covers regular, vegan, and gluten-free whoopie pies, so a mixed group can share one box without anyone missing out.
Cookies, coffee, and specialty lattes are on the menu too. Free Wi-Fi makes it handy for a work break.
The location inside a big office complex explains the schedule. It runs Tuesday through Friday, 8:30 AM to 4 PM, and is closed weekends and Mondays.
Can’t make it in person? Delivery is available.
On-site and street parking are free.
8. Jennifer Lee’s Gourmet Bakery Worcester, Worcester, MA
Food allergies often mean skipping the bakery case entirely. Jennifer Lee’s Gourmet Bakery in Worcester changes that, with baked goods made free of many common allergens.
The chocolate whoopie pie with chocolate frosting is the one to know. It is rich and deeply chocolatey, and it is hard to guess it is allergy-friendly.
The case also holds donuts, soft pretzels, blondies, cupcakes, bread, and cinnamon rolls. That variety is unusual for an allergen-conscious kitchen.
This is the kind of place I would send a friend who has been avoiding whoopie pies for years.
Weekday hours are 10 AM to 6 PM, while weekends open earlier at 7 AM and close at 3 PM. Delivery is offered, and a free parking lot sits at the Cambridge Street location.
From the North Shore to Cape Cod and out to Worcester, these bakeries show the whoopie pie is alive and well in Massachusetts. Pick a direction, bring a friend, and split a box.
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