One pie bakery on the Massachusetts coast opens at 5 a.m. and stays open 364 days a year. When the ferry docks nearby, the wait for a slice can stretch to half an hour.
I love that people line up for pie like it’s a concert ticket.
That shop is only one stop on this list. Another serves deep-dish apple pie inside an inn that dates back to 1707.
A third bakes a salted caramel apple pie, which sounds like a dare I would happily accept.
Pumpkin spice grabs the autumn spotlight every year. Apple pie quietly wins the long game, showing up at farm stands, diners, bakeries, and colonial inns across the state.
I can’t stop thinking about the range here. Flaky crusts, crumb toppings, Dutch apple, and hand pies you can eat while walking.
I’d keep a fork in my glove box for the whole season.
1. Longfellow’s Wayside Inn, Sudbury, MA
Few desserts come with a backstory that starts in 1707. At this Sudbury landmark, your slice of deep-dish apple pie arrives inside one of the oldest inns in Massachusetts.
The building still works as an inn, with rooms filled with antiques. Downstairs, the restaurant serves lunch and dinner with full table service and a fireplace that suits a chilly afternoon.
The deep-dish apple pie is the star for this list. It’s thick, generous, and exactly the kind of dessert that makes skipping pumpkin spice feel smart.
Can’t decide on one sweet? The strawberry shortcake also earns praise, and the cream puffs are another popular pick.
Save room by planning your meal with care. The menu leans toward comfort food, and the shrimp casserole is one of the dishes people know it for.
The setting is a big part of the fun here. Old wooden rooms, quiet corners, and a patio give you options depending on the weather.
Timing matters, so check the schedule before you go. The inn is closed Monday and Tuesday, and it serves lunch and dinner Wednesday through Sunday with a midday break most days.
Reservations are recommended for lunch, dinner, and brunch. Friday and Saturday evenings tend to be the busiest, so a weekday visit can feel calmer.
Parking is easy, with a free lot on site. That makes it simple to stretch your legs and wander the grounds after dessert.
Honestly, eating apple pie in a building older than the country feels a little like time travel. It’s tasty history, served on a plate.
Address: 72 Wayside Inn Rd, Sudbury, MA 01776
2. Pie in the Sky Bakery & Cafe, Woods Hole, MA
Ferry passengers in Woods Hole have a sweet little problem. When the boat docks, the line at this bakery can stretch 20 to 30 minutes.
Is the wait worth it? For apple pie fans, the answer leans toward yes, since the apple is a standout among the fruit pies.
The flavor here comes heavy on cinnamon. The crust isn’t the super flaky kind, so expect something sturdy that holds up to a thick filling.
Hours are wonderfully early. The doors open at 5 a.m. and stay open until 8 p.m., seven days a week.
Even better, the shop says it’s open 364 days a year. That’s commitment to pie that most of us can only dream about.
Coffee gets roasted in-house, which pairs nicely with a slice. Croissants also shine, including an almond croissant and a spinach feta version for savory moods.
Ordering happens at the counter, with seating inside and out. Takeout works well if you’re racing to catch the next boat to Martha’s Vineyard.
Plant-based eaters get options too. The menu includes full vegetarian and vegan choices, along with breakfast and lunch items.
Dogs are welcome at the outdoor seats. So your four-legged travel buddy can watch you eat pie with very sad eyes.
Reservations aren’t taken, so plan your arrival around the ferry schedule if you can. Mornings on weekends tend to be the busiest stretch.
Address: 10 Water St, Woods Hole, MA 02543
3. Helen’s Restaurant, Concord, MA
Homemade apple pie with a scoop of ice cream on top is the move at this Main Street favorite. Nobody has to twist your arm here.
Concord gives you plenty of reasons to visit, from history to bookish walks. A stop for pie and ice cream makes the day even better.
The restaurant is a casual bistro serving American food for breakfast, lunch, and dinner. Pies and ice cream are what it’s best known for, so dessert is not optional.
Apple pie leads the way, but blueberry pie is also on the dessert lineup. Ordering a slice of each and sharing sounds like solid teamwork.
The space is small and can feel tight. Portions run plentiful, though, so nobody leaves hungry.
Paying is easy here, since the restaurant accepts major credit and debit cards. That’s one less thing to worry about before ordering dessert.
Hours run from 8 a.m. to 7 p.m. on weekdays. On Saturday and Sunday, the kitchen closes at 3 p.m.
Weekend mornings and afternoons draw the biggest crowds. Weekday evenings are quieter if you want a slower slice.
Reservations aren’t accepted, so just show up. Takeout is available if you want to carry your pie on a stroll through town.
Vegetarians will find a full menu of options. It’s an easy pick for a group with different tastes and one shared love of dessert.
Address: 17 Main St, Concord, MA 01742
4. The Whately Inn, Whately, MA
Here’s a dinner where dessert comes included. At this 18th-century colonial home, the meal price covers appetizers, salads, and desserts.
Dessert is included with your entrée, giving you something sweet to look forward to after dinner. The exact choices can vary, so ask about the apple desserts before ordering.
The Whately Inn leans French in its cooking. It’s known for fine dining in a historic setting, with a banquet hall and simple lodging on the property.
Swordfish is one of the menu highlights. Vegetarians also get a full menu, so nobody at the table is stuck with a side salad.
A fireplace adds charm on colder nights. The mood stays quiet and romantic, which makes this a strong pick for a date or anniversary.
Western Massachusetts roads in fall are a treat on their own. Pairing a scenic drive with apple crumble pie feels like a smart seasonal plan.
Plan around the schedule, since this is a dinner spot. It’s closed Monday and Tuesday and opens at 4 p.m.
Wednesday through Saturday.
Sunday hours start earlier, at 1 p.m., and wrap up at 7 p.m. That’s a nice window for an early supper with the family.
Reservations are recommended for dinner. Saturday evenings tend to fill up first.
Takeout and curbside pickup are offered too. Still, eating dessert in a centuries-old dining room seems like half the reason to come.
Address: 193 Chestnut Plain Rd, Whately, MA 01093
5. Salem Cross Inn, West Brookfield, MA
Six hundred acres of farmland surround this 1700s inn. That’s a lot of room for an appetite to build before dessert.
Deep-dish apple pie is one of the traditional desserts served here. The inn also makes its chowder and hosts special Fireplace Feasts featuring prime rib cooked over an open hearth.
Locally sourced American food is the focus. Maple-glazed chicken, known on the menu as Maple Jack Chicken, is a signature dish.
The dining rooms feature giant fireplaces. Rustic beams and old charm give the place a festive, storybook feel.
So why save room for pie? Because a farm-to-table meal ending with a house-specific apple pie is the kind of combo that sticks in your memory.
Hours are limited, so mark your calendar. It’s closed Monday through Wednesday, open 4 to 8 p.m.
Thursday through Saturday, and noon to 5 p.m. on Sunday.
Reservations are recommended for dinner. Friday and Saturday evenings draw the biggest crowds, while Thursday afternoons are calmer.
Vegans and vegetarians get full menus here. That’s a nice surprise at a country inn known for prime rib.
Parking is plentiful, with a free lot on site. The rural setting in central Massachusetts makes it a fine fall drive from Worcester or Springfield.
Takeout and curbside pickup are available. Grabbing a pie for later might be the smartest decision you make all weekend.
Address: 260 W Main St, West Brookfield, MA 01585
6. Crabapple’s, Falmouth, MA
A restaurant named after a tiny tart apple had better nail its apple pie. Good news: this Falmouth spot does.
Homemade pies are a big part of the appeal. The apple version gets called out as a must-try, so plan your order around it.
The menu leans heavily on local seafood. Seafood chowder is a favorite, and a seafood pie with coleslaw and potato is another savory option.
Massive windows dominate the straightforward dining room. Natural light pours in, which makes a breakfast slice feel almost healthy.
Wait, pie for breakfast? Doors open at 7:30 a.m. daily, and nobody is checking what you order first.
Breakfast is the most popular meal here. Sunday mornings get especially busy, so arriving early helps.
Closing times change through the week. It closes at 3 p.m.
Sunday through Wednesday and stays open until 9 p.m. Thursday through Saturday.
Reservations aren’t accepted, so just walk in. Service tends to move quickly, which helps when tables turn over.
Outdoor seating and takeout are both available. Grabbing a whole pie for a Cape Cod beach picnic sounds like a plan worth making.
Plenty of parking is usually easy to find. That’s a small miracle in a Massachusetts beach town during peak season.
Address: 553 Palmer Ave, Falmouth, MA 02540
7. Deluxe Town Diner, Watertown, MA
Some praise sets a high bar, and this Watertown diner earns a big one. Its apple pie has been compared to something Julia Child might have baked herself.
Fun fact: Julia Child lived in nearby Cambridge for decades. So that comparison carries a little extra local weight.
Order the pie à la mode. Warm apples and melting ice cream are a diner classic for good reason.
The diner itself feels like a throwback, small and quaint. Breakfast is served all day, along with sandwiches, burgers, and comfort food.
The menu runs large. Highlights include challah French toast, johnny cakes, steak and eggs, and crab cake Benedict with home fries.
Portions come generous, so pacing matters. You’ll want to leave space for that slice at the end.
Hours stay steady from 8 a.m. to 8 p.m., seven days a week. That consistency makes it easy to plan a pie run.
Weekend mornings bring the biggest crowds. Evenings are much quieter if you want pie without the wait.
Parking can be tricky to find nearby. Leave a few extra minutes for circling the block.
A braille menu is available, which is a thoughtful touch. Vegetarians also get a full menu to choose from.
Address: 627 Mt Auburn St, Watertown, MA 02472
8. The Apple Place, East Longmeadow, MA
With a name like The Apple Place, expectations are basically built in. This East Longmeadow bakery and creamery lives up to its label.
Homemade apple pie shares the spotlight with cider donuts and homemade ice cream. Together, they form a fall trio that’s hard to beat.
Why choose just one? A slice of pie topped with house-made ice cream, plus a donut for the road, seems like reasonable math.
The setting has a rustic family feel. Farm animals and a playset give kids something to do while grown-ups pick out pies.
This is a quick visit kind of stop. Think grab-and-go treats rather than a long sit-down meal.
Coffee is available, along with breakfast items. Pairing a hot cup with a cider donut on a cool morning sounds perfect.
Hours run 9 a.m. to 7 p.m. most days, and until 8 p.m. on Friday and Saturday. It’s closed on Tuesday, so don’t get your heart set on a Tuesday pie.
Weekend afternoons and evenings tend to get the busiest. Weekday mornings are much quieter.
Prices can run a little higher than some spots. Still, the ice cream and apple pies have a strong reputation as some of the best in the area.
A free parking lot makes stopping easy. It’s a handy detour if you’re near Springfield or the Connecticut border.
Address: 540 Somers Rd #83, East Longmeadow, MA 01028
9. Rice Fruit Farm, Wilbraham, MA
At 6 a.m., most bakeries are still yawning. This historic Wilbraham farm stand is already open and selling pies.
Rice Fruit Farm works out of a remodeled barn. It feels like a throwback to an older style of roadside shopping.
Pies are a headline item. Apple joins other fruit pies, along with chocolate cream and pecan.
The apple pie has earned serious praise, even being called the best pie someone ever had. That’s a strong claim, and a great excuse to test it yourself.
Muffin tops are another popular pick. Yes, it’s the best part of the muffin, sold on its own.
Breakfast sandwiches make this a morning stop too. Homemade ice cream covers the afternoon cravings.
Local produce fills the farm stand. You can grab fruits and vegetables alongside your dessert and call it a balanced trip.
Hours are generous and early. It opens at 6 a.m. daily, closing at 7 p.m. most nights and 8 p.m. on Friday and Saturday.
Weekends bring steady crowds from morning to evening. Weekdays offer a calmer visit.
Dine-in and takeout are both options. Free parking and Wi-Fi round out a simple, easy stop in western Massachusetts.
Address: 757 Main St, Wilbraham, MA 01095
10. Marion’s Pie Shop, Chatham, MA
Flaky, buttery, and not too sweet is a hard balance to strike. Marion’s Pie Shop pulls it off with its apple pie.
The Chatham counter shop is all about house-made pies. Dutch apple is a fan favorite, with a crumbly topping that adds crunch.
Hand pies deserve their own shout-out. Apple and blueberry versions are considered must-haves, with homemade crusts that hold up beautifully.
Want more than pie? Turnovers, muffins, and coffeecake muffins also line the counter.
Savory eaters aren’t left out. Comfort foods like lasagna are available to take home for dinner.
This is strictly a takeout shop. There’s no dine-in seating and no restroom, so plan your visit accordingly.
A hand pie makes a great walking snack around Cape Cod. Pack a whole pie too, because one slice rarely feels like enough.
Hours run 8 a.m. to 5 p.m. Tuesday through Saturday.
Sunday closes at 4 p.m., and Monday is a day off.
The shop stays busy through much of the week. Arriving early gives you the best shot at your favorite flavor.
Parking includes a free lot. That’s handy on the busy stretch of Main Street heading toward Chatham’s town center.
Address: 2022 Main St, Chatham, MA 02633
11. Petsi Pies, Somerville, MA
Salted caramel apple pie sounds like something a dessert genius dreamed up. Petsi Pies makes it real in Somerville.
The apples cook down to just the right softness. Flaky pastry and a salted caramel spiced filling wrap it up nicely.
Prefer a classic? The apple crumb pie offers soft apples under a buttery crumb topping.
Other pies fill out the case, including cherry and Mississippi mud. Savory pies, cookies, cupcakes, and pastries round out the menu.
The shop is small, with just a few tables. Most people treat it as a quick stop.
Takeout and delivery are both available. Grabbing a whole pie for a dinner party might make you the most popular guest there.
Hours run 8 a.m. to 5 p.m. on weekdays. Weekends start at 9 a.m. and wrap up at 3 p.m.
Friday mornings and afternoons are the busiest. Weekend mornings tend to be calmer, which is great news for lazy risers.
Coffee is available to pair with your slice. There’s no restroom, so keep that in mind on a longer outing.
Street parking is free in the area. Beacon Street sits close to the Cambridge line, making this easy to pair with a city day.
Address: 285 Beacon St, Somerville, MA 02143
12. Flour Bakery + Cafe, Boston, MA
Right in the shadow of the Prudential Center, this bakery offers a sweet break from city errands. Apple pie is one smart reason to stop.
Flour Bakery + Cafe is known for artisan pastries and made-to-order sandwiches. Classic and creative treats share the pastry case.
The apple pie makes a fine slice to enjoy in-store. Sitting down for a rest with pie and coffee is a solid Back Bay move.
Of course, this is Boston, so another pie gets attention. The Boston cream pie is a big favorite, along with raspberry lemon cake.
Fun fact: Boston cream pie is actually a cake. Massachusetts even named it the official state dessert.
Pizza is on the menu too. That makes it easy to build a full meal before dessert.
Hours run 7 a.m. to 7 p.m. on weekdays. Weekends go from 8 a.m. to 6 p.m.
Sunday afternoons and Saturday mornings tend to be busy. Monday evenings are the quietest time.
Dine-in, takeout, and delivery are all options. Free Wi-Fi makes it a handy place to sit with a laptop and a slice.
The location is a short walk from Copley Square and the Prudential Center. Street parking exists, but transit is often the easier choice.
Address: 30 Dalton St, Boston, MA 02115
13. Ever So Humble Pie Co, East Walpole, MA
Humble is in the name, but these pies have plenty to brag about. Ever So Humble Pie Co in East Walpole is a pie lover’s playground.
Apple pie leads the way, and the apple crumb pie is often called even better. Trying both seems like the only fair way to settle it.
The selection is huge, covering sweet and savory pies. They come in different sizes, from small treats to full family desserts.
Ready-to-bake pies are a big feature here. You can take one home and fill your kitchen with that fresh-baked smell yourself.
Fresh-baked scones make a great snack while you shop. Coffee is available to go with them.
The pies use high-quality ingredients. Staff are known for being helpful when you’re stuck choosing between flavors.
Hours are short, so timing is key. It’s open 8 a.m. to 4 p.m.
Tuesday through Friday and 8 a.m. to noon on Saturday.
Sunday and Monday are closed. Plan a weekday or Saturday morning run so you don’t miss out.
A free parking lot makes stopping quick and easy. This is a grab-and-go shop rather than a sit-down spot.
Ending a Massachusetts pie tour here feels right. After a dozen great slices, a little humility is a sweet way to finish.
Address: 153 Washington St, East Walpole, MA 02032
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