After years (and I mean years!) of Gilmore Girls themed travel, I have put together the absolutely PERFECT 1-week New England road trip to ALL of the GG places!
This road trip hits up:
- The town that inspired Stars Hollow
- The places Amy Sherman-Palladino visited on her own trip
- Real life places mentioned in the show
- The actual small town seen at the beginning of EVERY episode
This trip passes through Massachusetts, Connecticut, and Vermont, to see as many Gilmore Girls places as possible (and it only takes one week!).
It’s jam packed with coffee, donuts, bookshops and quirky museums. Plus, if you have more than one week, there are plenty of add-ons you can do!
So get ready for the absolute best Gilmore Girls New England Road Trip route!
What’s in this Article:
- Best Time of Year to Go
- Day 1: Boston
- Day 2: Harvard & Cape Cod
- Day 3: Martha’s Vineyard or Nantucket
- Day 4: New Haven & Yale University
- Day 5: Washington Depot & Hartford
- Day 6: South Royalton, VT
- Day 7: Back to Boston
Best Time of Year for a New England Road Trip
The best time of year to go is undoubtedly the fall (though anytime would be good: summer is beautiful, and Christmas is magical!).
If you want the best fall foliage, you will want to come in October. Mid-October is the best bet, though it varies every year, and even from state to state.
The best foliage in Vermont will be at the beginning of October, and the best foliage in Connecticut will be at the end of October (thus mid-October is the best!). But whenever you come will be magical.
Just avoid January-March, as that will be the worst weather and road conditions, and a lot of seasonal activities will be closed.
New England Road Trip Day 1: Boston
Boston is mentioned in the show on several occasions. It’s where Rory and Lorelei go for Sherri’s baby shower.
Even if you’re traveling with someone who doesn’t like Gilmore Girls, Boston is a super cool city, and fun to explore! If you have more time, you can add another day in Boston either at the beginning or the end of this trip.
For day 1, we won’t plan too much, as it’s also the travel/arrival day. Fly into Boston Logan Airport and pick up a rental car (or drive your own car, if you live close enough).
- Pro Tip: Be sure to grab some photo props & themed outfits from my Gilmore Girls gift guide before your trip!!
New England Road Trip Route:
Things to Do in Boston
Here are a few quick ideas to do on your day in Boston:
- Take a guided history tour
- Follow the Freedom Trail
- Wander through the Boston Common
- Get something to eat at Quincy Market
- Eat Boston Cream Pie!
- Visit the Boston Tea Party Ships & Museum
- Watch a game at Fenway Park
Where to Stay in Boston
Boston is such a cool city, with so many great places to stay. Here are a few ideas to get you started:
Day 2: Harvard & Cape Cod
The first stop of the day is Harvard, a spot Lorelei and Rory visited on their own (spontaneous) New England road trip, back in season 2.
After exploring Harvard, you will have a choice to stay in New Bedford, or drive all the way onto Cape Cod. New Bedford is closer, and will save driving time, but Cape Cod is more interesting, and closer for taking a ferry to Nantucket (Martha’s Vineyard ferry is the same for both).
Tour Harvard
You don’t have to be a potential student to tour Ivy league colleges! In fact, Harvard not only offers public tours of their campus, they also have a plethora of specific themed tours for all interests! Art tours, nature tours, museums tours, and more!
You can download self guided tours through their app, or sign up for one of the many daily student led tours of campus. Tours are free, but be sure to sign up online ahead of time.
Make sure you visit these sites while you’re on campus:
- Visit Harvard’s Peabody Museum
- Visit the Harvard Museum of Natural History
- Visit a donut shop on campus, or better yet, take a DONUT TOUR!
- Shop at the Harvard Bookstore
Drive to New Bedford or Cape Cod
As I mentioned above, you can choose to base yourself for the next two nights in either New Bedford or Cape Cod. If you stay on Cape Cod, you will want to stay near or south of Hyannis (where the ferry port is). Tomorrow we will take a ferry to either Martha’s Vineyard or Nantucket.
New Bedford:
- Less touristy
- Less things to do
- Closer for driving on Day 4
- Longer ferry ride to Nantucket
- Visit the Whaling Museum and Seamen’s Bethel
Cape Cod:
- More touristy
- More things to do!
- Further for driving on Day 4
- Shorter ferry ride on Day 3
- Also mentioned on Gilmore Girls!
- So many things to do on Cape Cod!
Where to Stay
Some places to stay in New Bedford:
If you choose to stay on Cape Cod, there are TONS of hotels and rentals to choose from! I would suggest staying near Hyannis (where the ferry port is), or somewhere west of there, although Yarmouth is a really nice area, and not too far past Hyannis.
Day 3: Nantucket or Martha’s Vineyard
Both Nantucket and Martha’s Vineyard come up in Gilmore Girls as places Emily and Richard (and Logan!) like to vacation. Logan, Rory, Luke and Lorelei spend a (fateful) weekend on Martha’s Vineyard in season 6, and Emily actually moves (#spoiler) to Nantucket at the end of the revival series.
If you have more time, you can visit both islands! But if you can only pick one, my choice is for Nantucket, as it is smaller and easier to see all the sites on a day trip.
I took a day trip from New Bedford to Nantucket with my cousins last fall, and I had so much fun! I can’t wait to go back and explore Martha’s Vineyard with them sometime…
Day Trip to Nantucket
Here are some Gilmore girls inspired things to do on a day trip to Nantucket:
- Get coffee
- Tour the Whaling Museum (where Emily volunteers!)
- Sit in Mitchell’s Book Corner’s cozy book corner!
- Wander through the downtown shops & galleries
- Get ice cream
- Visit Brant Point Lighthouse
- Relax on the beach
Day Trip to Martha’s Vineyard
The ferry to Martha’s Vineyard will either let you off in Vineyard Haven or Oak Bluffs. I think Oak Bluffs is the better choice for a day trip.
If you choose to visit Martha’s Vineyard, here are some of the best things to do:
- See the gingerbread cottages (Oak Bluffs)
- Ride the Flying Horses Carousel (Oak Bluffs)
- Go shopping (especially antiquing!)
- Explore coffee shops and bookstores
- Visit Jaws filming locations
- Visit the Martha’s Vineyard Museum (Vineyard Haven)
- Relax on the beach
Day 4: New Haven & Yale University
We’ve already toured Harvard University, so now it’s time to tour the one Rory actually went to!
Yale University is in New Haven, CT, which is about a 2 1/2 hour drive from New Bedford, or a 3 hour drive from Hyannis on Cape Cod. Free public tours of the campus are given weekdays at 1 pm.
Tour Yale University
You don’t have to take a tour to visit Yale, but it is helpful. You can learn interesting facts, and see parts of campus that are closed off to the public (like the statue of Dwight Woolsey, where you can touch the toe!).
If you want to do a tour, make sure to book it ahead of time. Tours start at the Mead Visitor Center at 1 pm.
- Good to Know: Tours are student led, and are only offered during the school year.
After (or before) your tour, be sure to check out some of the popular sites at Yale (that you might remember hearing about on the show!):
Explore New Haven
New Haven is a fun college town, with lots of great restaurants! Here are some other places to see in town, and the best places to eat (that Rory definitely would have frequented. At least… if she had money!):
- The Shops at Yale
- Atticus Bookstore Cafe
- Book Trader Cafe
- Grey Matter Books
- Donut Crazy
- Sherkaan Indian Street Food
- Louis’ Lunch
- Frank Pepe Pizza
- New Haven food trucks
- PEZ Visitor Center
Where to Stay in New Haven
If you can, try to stay right in downtown New Haven, so you can feel like you’re a part of campus and walk to all of the attractions! I stayed at an Airbnb apartment that was a 15 min. walk to downtown.
Day 5: Washington Depot & Hartford
Washington Depot is the small Connecticut town where the idea for Gilmore Girls came to be. Amy Sherman-Palladino was staying at the Mayflower Inn, just outside of town, when she developed the concept.
Before we go any further, let me just say that Washington Depot is not exactly like Stars Hollow. My first visit here was disappointing. On my second visit, I could see more of how it inspired the town.
That being said, I’ve been told that multiple towns around the area were conglomerated to create the fictional “Stars Hollow.” I’ve been to all of them, and written a detailed guide to all four Gilmore Girls towns in Connecticut. My personal favorite is New Milford.
Feel free to spend more time exploring all of the towns today, if you want.
Washington Depot & the Mayflower Inn
The Mayflower Inn was the inspiration for the Independence Inn on Gilmore Girls. It is expensive to stay in, but you can stop by for breakfast or lunch! Be sure to make reservations ahead of time. Then spend some time exploring their beautiful grounds.
Stop in little Washington Depot, CT. There is not a lot to see here, but there are a few shops worth exploring:
- Town green
- The Po Cafe
- Marty’s Cafe
- The Pantry
- Five Janes Boutique
- Hickory Stick Bookshop
- Washington Food Market
- Henry David Thoreau footbridge
Hartford & the Mark Twain House
If you want to, you can spend more time exploring the small towns near Washington, but definitely try to make time for the Mark Twain House in Hartford at some point (you could also tour the house tomorrow morning, if you wanted more time to explore the small towns today).
- Bonus: You can stop at Luke’s Donut Shop on your way from Washington to Hartford!
Amy Sherman-Palladino traveled to Connecticut to see the Mark Twain House in Hartford (also the home of Emily and Richard Gilmore). It is definitely worth a visit, especially if you do the costumed actor tour!
You can also visit the Harriet Beecher Stowe House right next door. Rory would be so excited!
Have dinner at one of the international restaurants just down the street, or pop over to the Old Wethersfield neighborhood, which looks just like Stars Hollow!
Where to Stay in Hartford
One of the best places to stay in Hartford would be a local inn in Old Wethersfield, a Stars Hollow-esque community just outside of the city. If you like city life, you could also find a hotel downtown. Or maybe find a cozy airbnb like this adorable cottage where I stayed!
Day 6: South Royalton, VT
It’s going to be about a 2 1/2 hour drive from Hartford to South Royalton, VT. There is not a ton to do in South Royalton (though there are lots of things to do nearby), so you can spend more time in Hartford this morning if you want.
As I said above, you could spend more time exploring the Stars Hollow towns yesterday, and tour the Mark Twain House this morning, if that works better for you.
- Bonus: It would add 45 min. to your driving time, but if The Better Bean in Monson, MA is doing their Gilmore Girls menu, you could stop here on the way to Vermont. Last year they did it for the month of September, and I seriously debated leaving at 5 am to get to Monson in time to try one of the drinks!
Now… why are we visiting South Royalton?? What in the world does it have to do with Gilmore Girls??
- Fun Fact: South Royalton, VT is the town seen in the opening credits of Gilmore Girls.
Explore South Royalton
South Royalton is a small town with not a lot going on. It is the home of the Vermont Law School, but their campus is a tad bit smaller than Yale or Harvard. And they even have a bookstore! But all the books are law text books… although you can get cutesy gifts, coffee or a Vermont Law School hoodie.
Here are the things to do in South Royalton:
- Get coffee at First Branch Coffee
- Shop in the local market
- Browse the gifts in the bookstore
- Eat at the local diner
- Get a burger
- Get tacos (& beer)
- Enjoy the gazebo and town green
Other Things to Do in Vermont
That pretty much covers South Royalton. But since you’re in Vermont, there is so much more you can do!
Here are a few ideas of other things to do that are fairly close by. My South Royalton guide has more detailed information.
- Sugarbush Farm
- Find covered bridges (there are A LOT)
- Billings Farm and Museum
- King Arthur Flour Flagship Store & Cafe
- Hike the Quechee Gorge
Where to Stay in Vermont
Unfortunately, you can’t stay right in South Royalton, but there are a lot of cute places to stay nearby! The best town to stay in would be Woodstock, VT. It’s super cute and close to South Royalton (I stayed in Stowe, VT, which is a great place to stay if you are extending your New England road trip).
New England Road Trip Day 7: Back to Boston
If you have more time, you can head up to Stowe, VT. Or you can add more time in Boston, or anywhere else on the trip that you may have wanted to see more.
But to keep this road trip to a week so that you can get back to…gross… “real life,” this is the day we have to drive 2 1/2 hours back to Boston.
Depending on your time table, you can fly back home from Boston this afternoon, or spend the day in Boston and fly out tomorrow morning.
I hope you enjoyed your Gilmore Girls New England road trip!
Further Reading:
If you have more time to explore Connecticut and the New England area, here are some helpful guides:
- Real Life Towns Like Stars Hollow (not just in New England!)
- 3 Gilmore Girls Road Trip Itineraries-For Connecticut, Canada and California
- The Best Things to Do in Connecticut
- Gilmore Girls Towns in Canada (where they filmed episode 1!)
- Things No One Tells You About Stowe, VT
Any more questions:
If you have any questions about planning a Gilmore Girls New England Road Trip, or any other suggestions of places to visit, feel free to email me or comment below.
Planning a New England road trip:
Save one of the pins below for future trip planning:
You might also like:
- A Gilmore Girls Day Trip to Nantucket
- How to Visit New Haven Like a Gilmore Girl
- Gilmore Girls Towns in Connecticut
- The Best Things to Do in Connecticut
- Real Life Towns Like Stars Hollow
- A Gilmore Girls Guide to South Royalton, VT
- Gilmore Girls Gift Guide
Julia is a travel blogger with a Bachelor’s Degree in photography from Indiana Wesleyan University. She worked as a professional photo-retoucher for seven and a half years, before leaving the company to work in the travel industry. She now works at a historic 1800’s hotel. When she’s not working, she’s reading fantasy novels or classic literature, and planning trips to magical destinations.
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