Blur Effect
Photo of AI-Magellan
27 Aug 2024
Edit Trip Edit
Bookmark TripSave

Connecticut Day Trip Itinerary for Fall

Autumn Adventure in Connecticut

Embark on a picturesque day trip through the enchanting landscapes of Connecticut this fall. Your journey begins at Gillette Castle State Park, where you can explore the unique medieval-style castle constructed by actor William Gillette, marvel at stunning scenic views, and wander along the park’s beautiful hiking trails.

Next, head to Devil's Hopyard State Park, a haven for nature enthusiasts. Here, you’ll experience breathtaking waterfalls and captivating legends associated with its name. The picturesque hiking trails offer an excellent opportunity to immerse yourself in the tranquility of nature.

Your adventure continues with a visit to the Essex Steam Train & Riverboat. Enjoy a nostalgic steam train ride through the scenic Connecticut River Valley. The experience is further enriched by a riverboat cruise that showcases the vibrant fall foliage along the riverbanks, making it a perfect destination for photography and relaxation.

Delve into America’s maritime history at the Mystic Seaport Museum. This expansive museum offers a fascinating glimpse into the past with its collection of historic ships, interactive exhibits, and a meticulously recreated 19th-century coastal village. It’s an educational yet entertaining stop for all ages.

Conclude your trip with a visit to Sleepy Hollow Farm & Orchard. Here, you can indulge in the quintessential fall experience by picking your own apples and enjoying farm-fresh produce. The beautiful autumn scenery provides a serene backdrop, rounding out your day with delightful memories of Connecticut’s fall splendor.

Plan your dream trip for Free with AI
Create a personalized itinerary effortlessly with our AI-powered planner.
Upgrade BackgroundUpgrade Picture

Recommended Explorations

  • Trip Point Pin1

    Gillette Castle State Park

    Explore the unique medieval-style castle built by actor William Gillette, enjoy scenic views, and hike the beautiful trails around the park.
    Open Google Maps Button
  • Trip Point Pin2

    Devil's Hopyard State Park

    Experience breathtaking waterfalls, picturesque hiking trails, and the captivating legend of the Devil’s Hopyard name.
    Open Google Maps Button
  • Trip Point Pin3

    Essex Steam Train & Riverboat

    Enjoy a historic steam train ride through scenic Connecticut River Valley, followed by a riverboat cruise offering picturesque fall foliage views.
    Open Google Maps Button
  • Trip Point Pin4

    Mystic Seaport Museum

    Discover America's maritime heritage at the largest maritime museum in the United States, featuring historic ships, exhibits, and a recreated 19th-century coastal village.
    Open Google Maps Button
  • Trip Point Pin5

    Sleepy Hollow Farm & Orchard

    Immerse yourself in the quintessential fall experience by picking your own apples, enjoying farm-fresh produce, and taking in the beautiful autumn scenery.
    Open Google Maps Button

Local Events & Happenings


Music for Your Journey


    Tasty Picks


    Stay Recommendations

    • Hotel Icon

      Treehouse Retreat at Winvian Farm, Morris, Connecticut

      Treehouse Retreat at Winvian Farm, Morris, Connecticut

      Located in Morris, this unique resort offers luxury cottages, each designed with a different whimsical theme, set on a beautiful 113-acre property.
      Picture for Treehouse Retreat at Winvian Farm, Morris, Connecticut
    • Hotel Icon

      Saybrook Point Resort & Marina

      Saybrook Point Resort & Marina

      Situated in Old Saybrook, this resort features waterfront views, a lighthouse suite, and stunning New England charm.
      Picture for Saybrook Point Resort & Marina
    • Hotel Icon

      The Study at Yale, New Haven

      The Study at Yale, New Haven

      Located in New Haven, this sophisticated boutique hotel offers scholarly decor with modern amenities, perfect for a culturally enriching stay.
      Picture for The Study at Yale, New Haven
    • Spicer Mansion

      This elegant boutique hotel in Mystic offers Gilded Age luxury and fine dining in a beautifully restored historic mansion.
      Picture for Spicer Mansion
    • Hotel Icon

      The Inn at Stonington

      The Inn at Stonington

      Situated in the picturesque village of Stonington, this charming inn offers waterfront views, cozy rooms, and a quintessential New England experience.
      Picture for The Inn at Stonington