Apple Picking and Pumpkin Picking in The Boston Area

Oct 25, 2021

apple and pumpkin picking

Fall favorite activities in the New England area can be summed up into four words: “apple and pumpkin picking.” Our Seaport district hotel gives you prime access to the wonders of the city and day trip escapes outside the city, allowing you and your family to make the most of New England’s cherished autumnal season. Read on to learn more about the best apple and pumpkin picking spots in and around the Boston area.

Apple Picking

Good ole fashion apple picking is a quaint and relaxing activity for people of all ages to enjoy. With ample orchards to choose from, you’ll be sure to find the one perfect for you and your group. From hayrides to farmstands, here are the features we love most about these awesome apple orchards.

Belkin Family Lookout Farm

Located in South Natick, only 30 minutes outside of Boston, this orchard is one of the oldest farms in the country. But don’t worry, they’re still thriving with some of the best selections of crispy, sweet apples ripe for the picking. And after you’re done apple picking, stop at The Lookout—an outdoor dining escape offering up a menu of craft ciders and beers for a post-pick cooldown. This season will require reservations for U-Pick activities, so be sure to check the website for rules and available times.

Dowse Orchards

Spanning more than 50 acres, with dozens of apple varieties to choose from, this Sherborn-based orchard can stock you up with all of your seasonal favorites. Visit their roadside farm stand to get your hands on some of their sweet homemade cider.

Brooksby Farm

Only a mere 35 minutes from Boston, located in the historic city of Peabody, is Brooksby Farms. In addition to their wide variety of seasonal fruits ripe for the picking (including apples and pumpkins!), Brooksby is also home to its famous onsite bakery that’s known for whipping up some of the tastiest treats around including apple cider donuts, muffins, and monkey bread. For details on safety guidelines, visit the farm’s website.

Tougas Family Farm

A little further away from the city but worth the drive, Tougas Family Farm, located in Northborough, boasts various fruits making it plentiful in the picking department year-round. Also found on site is their popular barnyard, playground, and farm kitchen to explore after you finish conquering the fields. Stop by the store for an order of apple cider donuts topped with rich and creamy Tougas Farm Kitchen’s ice cream for a successful day in the books.

Pumpkin Picking

Pick your own pumpkin or festive gourd straight from the patch at one of these exciting and abundant pumpkin patches!

Belkin Family Lookout Farms

No surprise, in addition to making our apple picking, Lookout Farms also boasts an exceptional pumpkin picking experience. Hop aboard the farm train to head out to the pumpkin field, where they grow around 25,000 pumpkins each season, and scope out your perfect pick.

Boston Hill Farm

For over twelve generations, this family-run farm has provided visitors with a quintessential New England autumn experience. Visitors are encouraged to grab a little red wagon and head out to the pumpkin field in search of their ideal festive gourd. In addition to pumpkin picking, guests are welcome to enjoy the petting zoo and even live music on the weekends.

Smolak Farms

Hop on a hayride and tour the farms, get lost in the corn maze, or get right down to pumpkin picking at this North Andover fall hotspot. Plus, activities for little ones are plentiful as the farm hosts a fall festival for kids every weekend during peak season. From cow train rides to face painting to carnival games and more, there’s plenty to do to occupy your time.           


Spend the Night at Our Hotel 

Our Hampton Inn Hotel is perfect for an overnight stay, while our Homewood Suites in the same building are perfect for families looking for apartment-style living. When you arrive at our hotel, you’ll be greeted by our new, custom-designed sculpture titled Arrival. This beautiful and unique work of art will welcome you into our space while paying homage to the area’s maritime roots and the flourishing creative community that makes the Seaport District so unique. Stay at our Seaport District Hotel to enjoy your fall visit to the beautiful New England area! 


Ready to book your stay at our new Seaport District hotel? Book now!


Book Now

Endless adventures by land or sea await you at the Hampton Inn and Homewood Suites by Hilton Boston Seaport. Book an elevated room or an apartment-style suite today!

Plan an Event

From corporate meetings to weddings and beyond, let us be the destination for your next event.


Boston EventsFamily Friendly Hotels