Vibrant Vistas & Picturesque Towns
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Vibrant Vistas & Picturesque Towns

Vibrant Vistas & Picturesque Towns

Regular price $65.00 USD
Sale Sold out

One trip is required per group.

* "PDF Instant Download" means the trip will be sent by email as a PDF document, and not by mail (the email is sent immediately after completing your purchase)


Hit the road and explore easy outdoor adventures, outstanding views and small towns that inspired Stars Hollow in Gilmore Girls.

Trip Highlights

  • A few small towns that inspired Stars Hollow, CT
  • Grab a beer in a truly unique (and spooky) destination
  • Lots of lookouts and easy outdoor adventures
  • Picturesque bridges and towers


This trip can be done Thursday to Sunday, year round. We do not recommend traveling Monday through Wednesday.


  • Families with older kids
  • Outdoor Adventurers
  • Couples
  • Photographers



Stroll a beautiful boardwalk with a coffee in hand to start your day of road tripping! Drive time to the second stop is 15 minutes.


A gorgeous footbridge or lookout tower worthy of Rapunzel awaits! We also recommend the gazebo that inspired Stars Hollow. Drive time to the third stop is 10 minutes.


Choose between a trail with gorgeous mountain views or grab a glass of wine at a historic farm. Drive time to the fourth stop is 25 minutes.


Whether you want to feel like Lorelai and Rory, another hike, picturesque bridge or to stop at an "abandoned" brewery, the choice is yours.



Can depart from

Hartford Area, New Haven Area, Springfield, MA Area

Before you go

What You'll Need to Bring

  • Bug Spray
  • Camera
  • Reusable Shopping Bags
  • Walking Shoes
  • Cash

Additional Details

  • Dog-Friendly


We're here to help!

From New Haven, CT:

2 hours and 40 minutes / 98 miles

From Hartford, CT:

2 hours and 40 minutes / 109 miles

From Springfield, MA:

3 hours and 20 minutes / 156 miles

From Yonkers, NY:

3 hours and 45 minutes / 171 miles

From Albany, NY:

4 hours and 20 minutes / 202 miles

*We recommend booking an overnight hotel if the driving distance is greater than 4 hours round-trip.

This trip is best done Thursday - Sunday, year round.

You can do this trip on Monday - Wednesday, but some options will be closed. At least one suggestion on each stop is open each day, year round.

We recommend leaving anytime between 9:30 and 10:00 am. The later you leave, the less time you may have to complete all of the stops.

This trip is pet-friendly! At every stop there will be at least one option for you to explore with your furry friend.

We recommended bringing up to 5 people on your surprise road trip.

If you're bringing a larger group, we highly recommend having one person in charge of booking reservations at the restaurants and attractions in advance. In your confirmation email, you'll receive a copy of the itinerary.

Some options on the fourth stop require a fee to enter. Free alternatives are presented as well.

After booking your trip, we'll send you a confirmation email with a few recommended accommodation options.

Customer Reviews

Based on 2 reviews
Fran C
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Awesome Day Trip!

My wife and I have always enjoyed taking rides to explore different areas around where we live. The "Guess Where Trip" was a new way for us to enjoy exploring, adding the mystery of not really knowing where we were going to explore. We loved opening the envelopes to see where we were headed next, found something to enjoy at every stop. We fully intend to get another trip this summer, when weather is a bit was a little chilly for us to include the walk/hike stops, other than for a quick stretch your legs, check out views, take pix. Highly recommend!!

Olha Lisowitch
Vibrant Vistas and Picturesque Towns

I got the trip for my family member. They love it a lot.
It was an amazing and very unique way to discover a new places in your neighborhood. Thank you so much!