A Bushel of Fall Fun

3-Day MetroWest Boston Fall Itinerary: A Bushel of Fall Fun

Looking for a classic New England fall getaway near Boston? This 3-day, 2-night MetroWest Boston itinerary combines farm-fresh treats, fall festivals, local food, historic traditions, and seasonal fun in Framingham, Westborough, Northborough, and Sudbury. From apple cider donuts and raspberry picking to Northborough AppleFest and a colonial-era celebration at the Wayside Inn, this fall weekend itinerary is packed with ways to experience autumn in MetroWest Massachusetts.

Itinerary at a Glance

Day 1: Alltown Fresh Framingham → DoubleTree Westborough
Day 2: Nourse Farm → Northborough AppleFest
Day 3: The Wayside Inn Colonial Faire & Fife and Drum Muster

Trip length: 3 days / 2 nights
Best for: Grandparents traveling with grandchildren, multigenerational families, and family weekend getaways
Best season: Late summer through fall
Location: MetroWest Boston, Massachusetts

DAY 1:

Grab a quick dinner at the curated marketplace at Alltown Fresh in Framingham on your way to the hotel. Choose from fresh favorites like a Mediterranean Bowl or Falafel Wrap, and don’t forget to treat yourself to a delicious smoothie!
Pick up your fresh-baked cookie when you check into the cozy DoubleTree in Westborough! Nestle in for a good night’s sleep in their comfortable, well-appointed rooms. Be sure to check out their fitness center and indoor swimming pool.

DAY 2:

Get your day going with a sweet breakfast treat. Head over to Nourse Farm for a New England Fall Classic, an apple cider donut! While you are there, pick some golden raspberries or a pumpkin or meet some of the locals such Phoebe Pips or Maple, their friendly goats!
Next, head over to the Northborough AppleFest! Indulge in a variety of delicious food trucks, look for some unique finds at their craft fair and be sure to stick around for the nighttime fireworks.

DAY 3:

Step back in time at the annual Colonial Faire & Fife and Drum Muster at the Wayside Inn! Travel back to the days just before the Revolutionary War, when local militia gathered twice a year in the fall and spring for drills and musters. Afterward, families joined the festivities for a day filled with music, games, good food, and plenty of merriment. Experience this lively tradition together and get a taste of what a New England gathering might have looked and sounded like centuries ago.

Sudbury Colonial Faire and Fife and Drum Muster

Frequently Asked Questions About Fall in MetroWest Boston

What can you do during a 3-day trip to MetroWest Boston?

A 3-day MetroWest Boston getaway can include visits to New England Botanic Garden, Unity Farm Sanctuary, Ashland State Park, local restaurants and shops, and the Upper Charles River Rail Trail. Staying in Natick also provides a convenient base for exploring several MetroWest communities.

What are some of the best things to do in MetroWest Boston in the fall?

Fall visitors can explore seasonal gardens, walk scenic trails, enjoy early foliage, visit local farms and sanctuaries, dine at independent restaurants, and explore charming MetroWest communities including Natick, Sherborn, Ashland, Holliston, and Boylston.

Is MetroWest Boston good for a fall weekend getaway?

Yes. MetroWest Boston is well suited for a fall weekend because visitors can combine outdoor activities, seasonal scenery, local dining, shopping, attractions, and comfortable accommodations within a relatively compact area.

What outdoor activities are included in this MetroWest itinerary?

This itinerary includes walking trails at Unity Farm Sanctuary, hiking at Ashland State Park, garden exploration at New England Botanic Garden, and walking or biking along the Upper Charles River Rail Trail in Holliston.

Where should you stay during this MetroWest Boston itinerary?

The Verve Hotel Boston Natick provides a central overnight option for this itinerary and offers convenient access to dining, shopping, and attractions throughout the MetroWest region.