Itinerary – New England Road Trip

In about a month, I’ll be embarking on a road trip to New England with Jason and my parents (you’ll notice I’ve strategically selected my company to avoid doing any driving myself!) Jay and I went on a mini trip to Rhode Island last summer, NE_Mapbut this time we’ll be checking out four cities we’ve never visited before. Since I’m a bit of an itinerary nerd, I find the actual planning and logistics part just about as much fun as the actual trip. Here’s a summary of our vacation, including the hotels, activities, estimated costs and estimated driving times for each stop. I’ll report back after the trip to let you all know how it went!

Day 0 (the night before doesn’t really count, does it?)

  • Parents arrive to stay overnight

Day 1

  • Leave early and drive to Hartford, CT (3 hr 15 min – 194 miles)
  • Explore Hartford
    • Mark Twain House (9:30am – 5:30pm)
    • Harriet Beecher Stowe House (9:30am – 5pm)
  • Stay: Residence Inn Hartford Windsor
    100 Dunfey Lane
    Windsor, CT 06095

Day 2

  • Leave early to head to Portland, ME (3 hr 15 min – 200 miles)
  • Explore Portlandsea-swirl-roll
    • Museum of Art (10am – 5pm)
    • Victoria Mansion (1pm – 4:45pm)
    • Wadsworth Longfellow House (12pm – 5pm)
    • South Worth Planetarium (in the college)
    • Lobster!!
  • Stay: Holiday Inn Express Biddeford
    45 Barra Rd
    Biddeford, ME 04005

Day 3

  • Sleep in and then drive to Portsmouth, NH (1 hr – 40 miles)
  • Explore Portsmouth
    • Prescott Park
    • Portsmouth Harbor Lighthouse
  • Drive to Salem, MA (1 hr – 47 miles)
    • House of the Seven Gables (10am – 7pm)
  • Drive to Sturbridge, CT (1 hr 30 min – 78 miles)
  • Stay: Hampton Inn Sturbridge
    328 Main St
    Sturbridge, CT 01566

Day 4

  • Explore Old Sturbridge Village
  • Drive to Southford Falls State Park (1 hr 30 min – 83 miles)
    • Hike the Falls Trail
  • Drive home (2 hr 30 min – 160 miles)

Trip Cost:

Residence Inn Hartford Windsor                            10,000 points per room
Holiday Inn Express Biddeford                                20,000 points per room
Hampton Inn Sturbridge                                           $106 or 16,000 points + $65
Mark Twain House & Harriet Beecher Stowe       $25 per person
Portland Museum of Art                                           $12 per person
Victoria Mansion                                                        $13.50 per person
Wadsworth Longfellow House                                 $14 per person
House of the Seven Gables                                       $12.50 per person
Gas                                                                                 $40 per person for entire trip
Meals                                                                             $50 per person per day ($200 total)
Total                                                                               ~$380 per person

Your turn! I’d love to hear suggestions for things to do / restaurants to check out in any of these cities!



  1. I was in Salem a few weeks ago. I love Salem!! It’s such a cute town, I want to live there! Best part: went in to a new and used bookstore …. Bought House of the Seven Gables in the “local authors” section! Coolest thing ever!
    Have fun; sounds like a great trip.

  2. Oh, ate at Life Alive. Highly recommend. All super fresh, super organic, and very cool environment. I won’t bother giving you the name of the sushi place, but it was some of the best sushi ever! And we had really good pizza, but I don’t know where it was from.

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