Date Day – Favorite Fall Activities

As you probably know, or if you’ve read any of the last few posts (7 Activities to Celebrate Autumn, Autumnal Equinox), the season of fall is our favorite! The weather is magically crisp and cool, the days become a bit shorter allowing us to see bold sunsets and sunrises, and the natural world around us bursts with the tones of the season.

One of our most favorite ways to celebrate the season is doing what most do this time of year: get dressed up in our favorite trendy fall finds, and head to an apple orchard to pick the freshest fruit still stuck to the trees. We call it our fall day, unique, I know. And it technically qualifies as a date day.

Favorite Fall Activity - apple picking in massachusetts, belkin family lookout farm

As a reminder, here are the terms to our dates that are held during the daylight hours:

  • The date chooser changes every other time
  • The date must involve at least one fun activity and include a plan for food
  • Dates that include alcohol are highly encouraged

This year, we decided the hang closer to home and experience the hidden gems that we have yet to find, this one being the Belkin Family Lookout Farm in Natick, Massachusetts (chosen by Sarah). By picking this spot we minimized travel time and maximized our hours outside in the orchards and fields. The Belkin Family Lookout has 180 acres where more than 60,000 fruit trees prosper. From peaches and pears, to the ever so popular apples and pumpkins, this farm offers something for even the most fall-adverse. This farm is also one of the oldest working farms in the U.S., boasting an establishment date of 1651.

But this legacy doesn’t mean old fashioned. No, this farm is truly a spectacle anytime of year, but definitely during October. Read on for a more in depth tale of how we spent our fall day!

After taking our time waking naturally on Saturday morning, we had an amazing breakfast at home featuring fluffy pancakes and crispy, thick-cut bacon. We then got ready for the day: it was a flawless fall day, a little overcast, but almost 70 degrees. At around 9:30am we were on our way. Our goal was to miss the family rush that tends to arrive around 10am.

After winding our way down the most idyllic driveway with old red barns on the left and big farmhouses on the right, interspersed with bright red-orange trees flanking the pavement, we parked out car in a big open field next to the u-pick market. We made our way to the ticket counters, which had areas for kiddos to play while the parents waited in line to purchase their day of fun. Though it cost us (only two adults) almost $70 for entry into the farm and a peck of apples, the excitement was building too much for us to care. Once the tram pulled up to take us to pick the all the apples we wanted (or at least enough to fill our bag), we hopped on and were on our way.

The little train tractors took us under canopies of grapes on paved paths, liming the amount of mud we had to trudge through to just the isles of apple trees. There are three stops on the tram route: the first had mcintosh, red delicious, and jonagolds; the second, asian pears, courtlands, and golden delicious; and the third featured macouns and more family friendly activities, including pony rides, a petting zoo, and even a courtyard where children can eat and where parents can sip on something a little stronger.

Favorite Fall Activity - apple picking in massachusetts, belkin family lookout farm

We had childish fun walking up and down the rows of apples trees, stopping to pick the ripest, but not overripe fruit. Once grabbing a drink in the courtyard around noon, and learning that they had a whole brewery on the premises, we headed back to the parking area to pick up some apple cider and fresh honey made on the farm. Oh, and don’t forget those apple cider donuts!

By the time we arrived at the taproom, we were starved! We picked out the eats we wanted and picked out four-packs of beverages we each wanted to enjoy in our own home. We also both chose a flight (one beer, one cider). Additionally, we were presently surprised by the quality of food we received and the spirits were definitely worth a second visit. See below for our food and drink choices and leave your favorite farms in the comments below.

Wine/Beer and Food Choices

Craft beer flight (an assortment of seasonal brews)

Cider flight (an assortment of seasonal brews)


Crispy brussel sprouts

Chipotle Ranch Chicken Tenders

Pretzel twists

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