Boardwalk leading to a beach.
Home / Trips / Coastal Connection

Coastal Connection

Coastal Connection

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)


Feel the ocean breeze in your hair as you go from beaches and boardwalks to independent shops and eateries. There are a few unusual surprises in this trip that will keep you on your toes! This is a great trip to do from the New Haven and Hartford area.

Trip Highlights

  • Small town charm
  • A spooky abandoned seaside spot
  • Sandy beaches and boardwalks
  • Buy some books at a one-of-a-kind shop
  • A 19th Century mansion turned art gallery


This trip can be done from Wednesday - Sunday, Spring - Fall.


  • Families with older kids
  • Couples
  • Girlfriend getaways
  • Beach bums



Start your day in one of Connecticut's oldest towns full of picturesque spots and cafes. Drive time to the second stop is 15 minutes.


Time to stretch your legs on 2 miles of sand or paved paths with lookouts. We also recommend a fantastic art gallery or boardwalk trail if you don't want to get sandy! Drive time to the third stop is 20 minutes.


We'll be shocked if you don't come home with something from this one-of-a-kind book store. If you're hungry for lunch there's a great brewery or cafe in town. Drive time to the fourth stop is 20 minutes.


Choose from a Hollywood famous town, beachside bliss, a seasonal cider spot or an abandoned seaside spot.



Can depart from

New Haven Area, Hartford Area, Providence Area, Springfield, MA Area

Before you go

What You'll Need to Bring

  • Bug Spray
  • Camera
  • Cash
  • Walking Shoes
  • Water
  • Reusable Shopping Bags
  • Road Trip Snacks
  • Bathing Suit
  • Beach Towel

Additional Details

  • Dog-Friendly
  • Accessible
  • Kid-Friendly


We're here to help!

  • From New Haven, CT:

2 hours and 15 minutes / 117 miles

  • From Hartford, CT:

2 hours and 48 minutes / 152 miles

  • From Providence, RI:

3 hours and 15 minutes / 186 miles

  • From Springfield, MA:

3 hours and 36 minutes / 202 miles

  • From Worcester, MA:

3 hours and 52 minutes / 228 miles

  • From Boston, MA*:

4 hours and 53 minutes / 288 miles

  • From Yonkers, NY*:

4 hours and 27 minutes / 246 miles

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

This trip can be done from Wednesday - Sunday, Spring - Fall.

We recommend leaving between 9:30 and 10:00 am if you’re in the New Haven Area. If you’re leaving from the Hartford Area, aim for 9:00 to 9:30 am.

This trip is pet-friendly! At every stop there will be at least one option for you to explore with your furry friend. Please be sure to keep your dog leashed at all times.

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 restaurants and attractions in advance. Please see the previous page for a copy of the digital itinerary.

First Stop: No fee

Second Stop: Our featured stop is free to explore! One optional state park is free for CT registered vehicles. An optional art gallery is $10-12 per person.

Third Stop: Our featured stop is free to explore! One optional state park is free for CT registered vehicles.

Fourth Stop: Some options require entrance fees. We've provided many free alternatives.

*Please note: gas, tolls, and food may be additional costs.

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

Customer Reviews

Be the first to write a review