Fall in Washington: A Day Trip Guide


Crisp autumn air, scenic vistas of the changing foliage, traditional apple picking, and indulging in all things pumpkin spice. The fall season is undoubtedly one of the most magnificent times to explore New England. We invite you to take a day trip to Washington, Connecticut to enjoy the perfectly charming small town experience – and we have the perfect guide for you! And even if you are lucky enough to call Washington your home, there’s always something to discover.


Heading into Washington

Washington is nestled in the rolling hills of Connecticut’s beautiful Litchfield County. Enjoy a scenic drive into town, whether you’re a local to Connecticut or an out-of-state visitor. Washington has a convenient travel distance of less than two hours from New York City and less than three hours from Boston.


As you arrive, start by heading towards the Washington Green where you can enjoy the pristine colonial architecture, church steeples, and storybook scenery. Across from the Green is the infinitely cozy Po Cafe, voted the “Best Spot for Coffee in New England” by Yankee Magazine. There you can linger and take in the view and special home-baked treat before you continue exploring for the day.


The Ultimate Apple Picking Experience

Next, head over to Averill Farm to enjoy the ultimate apple picking experience complete with delectable apple cider donuts, homemade jams and jellies and a selection of pumpkins, flowers, and pies. Averill Farm is a tenth generation family farm set on a gorgeous hilltop overlooking Litchfield Hills and a beloved fall tradition in Washington.


You can also find their famous apple cider donuts and abundant produce from area farms at the Washington Farmers Market at Judy Black Park on Saturdays from 10am-1pm.


A Scenic Autumn Escape

The five villages of Washington are crisscrossed with scenic roads and breathtaking vistas from which to view New England’s unsurpassed fall foliage. In fact, Washington is cited by U.S. News & World Report as one of the fifty towns across America with the most gorgeous fall foliage.


Drive through Washington’s most scenic roads to enjoy leaf-peeping from the comfort of your car or experience rolling hills of Litchfield County with KC&E Adventures’s self-guided e-bike experience! Get even closer to nature by exploring our abundant hiking trails and state parks that provide ideal fall foliage vantage points.


Delicious Fall Specials

After an eventful first half of your daytrip, make sure to enjoy a delicious lunch at the GW Tavern, The Owl Wine & Food Bar, or The Smithy Cafe where you can find outstanding seasonal specials on the menu along with specialty drinks to celebrate the fall season.


You can sit back and relax at these wonderful local restaurants or get it to-go to enjoy a fall picnic by Lake Waramaug or the New Preston Falls!

Washington Art Association Gallery @kenisebarnesfineart

Fall Art Inspiration at the Galleries

Washington is known for its incredible arts and cultural organizations, so be sure to take in the latest exhibits on display at the art galleries in town. Be inspired by the latest works at the Washington Art Association, KMR Arts, Judy Black Memorial Park and Gardens, and the Byrde + the b.


  • “House and Garden” Exhibit @ Washington Art Association – Through October 8th
  • Clayway Artist Studio Tour @ Will Talbot’s Studio – October 15th & 16th
  • Art @the Park: Lucas Reiner @ Judy Black Memorial Park and Gardens – Through October 23rd
  • Lucas Reiner’s “Figure/Ground” Exhibit @ KMR Arts – Through October 29th
  • Jeff Kellner’s “A Photographer’s Eye” Exhibit @ Byrde + the b – All season

Winding Down at the Vineyards

In the afternoon, take the time to sit back and relax with live music and wine tastings at Hopkins Vineyard and Spring Hill Vineyards.


Hopkins Vineyard offers wine flights, small bites, live music, and beautiful views overlooking Lake Waramaug. Live music is held on Saturdays from 3-6pm and Sundays from 2-5 pm.


At Spring Hill Vineyards, you can enjoy house wines by the glass or bottle and explore their unique setting, including the immersive Bee Brook Grotto art installation nested at the top of the repurposed Spring Hill Silo. The vineyard is open Saturdays and Sundays from 12pm to 5pm through Columbus Day.


Unique Tastes of Washington

Before you head home, make one last stop to celebrate your fall adventure in Washington with a cozy dinner at The White Horse Country Pub & Restaurant, The Community Table, Flemming’s Hidden Valley Restaurant, or any one of our incredible restaurants in town.


Whether you’re in the mood for a classic burger or more exotic cuisines, Washington has incredible options to choose from. And don’t forget to treat yourself to a special dessert, the cherry on top of a memorable day!

We hope you are able to enjoy a magnificent day trip to Washington this season!

For more ideas, take a look at some favorite fall activities from Washington locals:

  • kce_adventures Crisp mornings in front of the wood burning stove, changing colors, long e-bike rides through the foliage, pumpkin patches, apple picking….basically what *aren’t* we looking forward to?!
  • byalexandrabarnes Cider donuts! But that’s just the tip of the iceberg…
  • smcleathers Daily changes of the leaves, all the fall fun events, gathering friends outdoors by the fire
  • yankeeinconnecticut Back road driving and leaf peeping with @connecticutclassic


What else do you love to do in Washington in the fall season?
Let us know by tagging us @explorewashingtonct