My 6-Day New England Road Trip
No matter where the road takes me, it always seems to end with water, silence, and that feeling of having gone just far enough.
This week, a year ago, I spent six days on the road, looking for small towns, lighthouses, and coastlines, while chasing fall colors, sunsets, and lobster rolls! People often ask me where to go and what to see, so this week’s blog is going to take you along for the ride!
Here’s the route I took and the order in which I saw everything, just in case you’d like to try it, too.
Day 1 – Annville, PA → Mystic, CT
Route: Annville → Top of the 80s (PA) → Amenia (NY) → West Cornwall Covered Bridge (CT) → Mark Twain House & Museum (Hartford) → Mystic
Highlights:
• Leave before 9:00 AM and take coffee for the road… mountain views at Top of the 80s.
• Stop for gas in Amenia, NY, and stretch your legs. Wandering in the rain made this quirky town even more memorable. Check out the Four Brothers Drive-In.
• Quick photo stop at the West Cornwall Covered Bridge.
• Literary detour to the Mark Twain House & Museum.
• Sunset arrival in Mystic… harbor lights, calm water, and dinner at Chapter One (for lobster roll #1).
Even in the rain, this was a perfect route for all of these stops and even made the photos more interesting and moody.
📸 Photo Ops:
The view from Top of the 80s
West Cornwall Bridge
Arriving in Mystic just as the bridge lights come on and the sun sets.
Day 2 – Stonington/Mystic/Noank
Route: Local exploring
Highlights:
• Stonington Borough… pick up breakfast and coffee at Indulge Coffee Co. Then drive down to Stonington Point/Dubois Beach and enjoy your meal with a view.
• Stonington Lighthouse Museum… walk up from The Point to visit the Lighthouse Museum and climb the short stairwell to the top for sweeping views over the town and harbor.
• United Church of Stonington… while taking photos, a kind couple invited me inside for a peek. These are the moments I live for when traveling: connecting with locals and seeing the pride they have for their town.
• Mystic Seaport Museum… worth taking your time to wander and learn the history of the port and shipbuilding.
• Abbott’s Lobster in the Rough… a five-minute drive over to Noank for a late lunch and lobster roll #2 with gorgeous views over Mystic Harbor.
• Carson’s Store… a charming little country store that feels straight out of a Hallmark movie.
• Downtown Mystic… shop, people-watch, and hopefully see the bascule bridge in action. Dinner anywhere in town is a win, but for me, it was Chapter One again just for drinks and baseball.
• Inn at Mystic… this is where I chose to stay. A hotel with old-fashioned charm, harbor views, and a cozy restaurant. After an evening stroll through Mystic, it was back to the hotel bar, Rocks 21, for one last bite, a caramel appletini, and more baseball.
📸. Photo Ops:
Morning at the Seaport Museum: boats, rope, and sea air.
Stonington Borough’s stone walls, colorful shops, and lighthouse.
Lunch with a view at Abbott’s Lobster.
Day 3 – Rhode Island Coastline
Route: Mystic → Watch Hill → Jamestown → Beavertail State Park → Newport → back to Mystic
Highlights:
• Watch Hill Lighthouse & beach walk… a beautiful coastal town with immaculate homes and landscaping. You’ll park and walk to the lighthouse; worth every step. (Yes, Taylor Swift has a house here.)
• Jamestown/Beavertail Lighthouse… stop for breakfast and coffee at East Ferry Deli in Jamestown. Enjoy the view while eating out on the patio, or take your food to go and drive out to Beavertail State Park for stunning views over Narragansett Bay. Explore the cliffs around the lighthouse and just soak in the peacefulness of the Naragansett Bay. Check out the small museum or aquarium if they’re open.
• Newport
International Tennis Hall of Fame… even if you’re not a tennis fan, the history and architecture make it worth a stop.
Lunch at Midtown Oyster Bar… pumpkin-spice espresso martini + lobster roll #3!
Cliff Walk… this time I found the “40 Steps” and took my time. Do the walk… it’s gorgeous.
Castle Hill Lighthouse… my favorite lighthouse of all time. Arrive at sunset and you’ll understand why. It sits on the property of the Castle Hill Inn, so find your way there and park in their parking lot. You’ll need to hike up through the trees to get to the rocks, but once it opens up, you’ll see that beautiful little lighthouse.
Back to Mystic for another evening stroll downtown and lobster roll #4, because, why not? Topped it off with the best salted caramel gelato I’ve ever had!
📸 Photo Ops:
Watch Hill Lighthouse
Beavertail’s windy cliffs… worth every hair-out-of-place moment.
Newport’s Cliff Walk… the ocean never stops performing… oh, and the mansions!
Castle Hill Lighthouse… find the Castle Hill Inn, park in their lot, then hike up through the trees until it opens up at the rocks over the bay.
Day 4 – Cape Cod Drive
Route: Mystic → Olde Mistick Village → Sandwich → Barnstable → Brewster → Provincetown → Eastham → Hyannis
Highlights:
• Coffee + quick browse at Olde Mistick Village… I always stop at Sticky Situations to stock up on honey, vinegar, and olive oil. Then onward to a scenic drive along the bay side of the Cape.
• Sandwich, MA… grumbly tummy, so stopped for a breakfast sandwich and a coffee at the Snowy Owl Sandwich Shop… in Sandwich. Snowy Owl Coffee Roasters.
• West Barnstable Train Station… fun photo op and a peek into rail history.
• Stoney Brook Grist Mill & Museum… sunny afternoon walk and photo stop.
• Provincetown… drinks downtown, then Herring Cove Beach for sunset and photos of Race Point Lighthouse. The full moon rising behind me made it unforgettable.
• Eastham… dinner at The Lobster Shanty for lobster roll #5 before overnighting in Hyannis.
📸 Photo Ops:
Sunset on the Cape = a photographer’s dream.
Brewster Grist Mill
Provincetown streets alive with color.
Day 5 – Rockport/Gloucester
Route: Hyannis → Plymouth → Rockport → Folly Cove → Nashua
Highlights:
• Plymouth, MA… an unplanned stop at Pilgrim Memorial State Park to see Plymouth Rock, the Mayflower II, and grab breakfast at Carmen’s Café Nicole. (Update: currently closed)
• Rockport, MA… I was finally here and like a kid in a candy store with my camera. Needed another coffee at Brothers Brew to get me through the day, then off I went! Must photograph… the town shops, Motif #1, and the view of the harbor from the Rockport Breakwater. It’s a slow but easy walk across the rocks.
• Folly Cove / Virginia Lee Burton Cottage… rebuilt at the Lanesville Community Center to honor the beloved author/illustrator. Closed that day, but I was able to get some beautiful fall photos and peek in the windows. She is the inspiration behind all of my writing for children.
• Nashua, NH… dinner and baseball at Martha’s Exchange before overnighting — a long drive home tomorrow.
📸 Photo Ops:
Rockport reflections — picture-perfect New England.
The Mayflower II and Plymouth Rock.
The cottage where “The Little House” was born.
Day 6 – The Drive Home
Route: Nashua → Peterborough → Brattleboro → Creamery Covered Bridge → Annville
Highlights:
• Peterborough… I knew it was a long drive home from Nashua, so I didn’t plan much except a stop in Peterborough… peaceful scenes and fall color everywhere.
• Brattleboro… the last stop of the trip before heading home. A photo shoot of the town, stepping across the border from New Hampshire to Vermont, and the Creamery Covered Bridge finished off this New England loop.
**I must mention the Brattleboro Food Co-op… a perfect place to grab healthy food and snacks for the long drive home.
📸 Photo Ops:
Downtown Peterborough
The VT/NH State Line
Creamery Covered Bridge
Closing Notes
Six days, six states, five lobster rolls, and countless small-town stories.
If you’ve been craving a fall road trip, this loop has everything I love… winding roads, back-porch coffee stops, and towns that make you slow down. From the salt air in Mystic to the windy cliffs of Beavertail and the quiet hum of Rockport’s harbor, every stop still lingers with me long after the suitcase is unpacked.
Every road trip teaches me something new… about the world and about myself. Is there a place that still lingers with you long after you’ve unpacked the suitcase?
The view from my room at The Inn at Mystic.
