The Perfect Fall Foliage Road Trip
We occasionally throw in a bucket-list road trip between all of our (almost) free flights. The road-trip itself was amazing but there were a lot of factors impacting the changing of the fall leaves like level of rain-fall and current temperatures. We aimed for the first week in October, but that year in particular, I think the second week would have been slightly better.
Day 1: Make your way to Pittsburgh, Pennsylvania
One of the best views of Pittsburgh comes from driving through the Fort Pitt Tunnel, which offers a skyline view of Pittsburgh.
Where to stay: Fairfield Inn & Suites Pittsburgh Downtown
Dog friendly and parking available nearby (for an extra fee).
Where to eat
We arrived later in the evening, but we did make time for breakfast and highly recommend Gas Street Coffee. Great coffee and breakfast options and they were dog friendly too! A quick walk from the hotel.
Day 2: Pittsburgh, Pennsylvania to Catskills, New York
Easily one of my favorite stops on our journey. The park near the hotel was absolutely perfect for a slow meander to admire the fall leaves and stretch our legs.
Where to stay: Hotel Vienna, Windham, New York
This hotel was just what we were looking for! Clean and spacious with a pool and sauna on-site and most importantly, right next to a stunning park that was simply beautiful.
Where to eat:
Brandywine - Old Italian restaurant with the best homemade, from scratch daily marinara sauce we've had this side of Italy.
Zach’s Place - Great local's bar with the friendliest people. Zack's your bartender and head chef.
Days 3 - 5: Catskills, New York, to Boston, Massachusetts
For all the Gilmore Girl fans out there, I highly recommend stopping or even staying at the Mayflower Inn & Spa, Auberge Resorts Collection. This is the Inn that inspired Gilmore Girls. We only stopped by, but the Inn looked absolutely incredible. A perfect place to enjoy the fall weather with a 5-star experience.
Where to stay:
5-Star luxury Inn, absolutely beautiful
If this is your choice, PLEASE reach out to me! As a travel advisor, I can sometimes arrange better discounts, and other perks .
If you've ever stayed at a Moxy hotel, then you know their rooms small but functional. They allowed us to bring our dog to their bar which was fantastic since the room is cramped with a dog. Peloton and Treadmills, weights, etc.
Where to eat:
Sally’s Apizza - Stop in for lunch and enjoy the cozy small town vibes of New Haven. Take your pizza to go and eat in the park nearby.
Neptune Oyster - The line was crazy long, and the prices were daunting, but this was the best meal we had on the trip. No question.
Union Oyster House - The oldest restaurant with in-continuous service in the US. Enjoy the fun history that covers the walls and order the scallops.
What to do: Boston
Freedom Trail - Pro Tip: download the National Park Service App and take the free guided walking tour. Just follow along the brick path and listen to the history through the app.
Public Garden - Beautiful park with swans. Enjoy, explore and maybe find the Good Will Hunting bench.
Charles River Esplanade - Long trail the runs along the river. Its a beautiful place for a long walk or run. Also runs along Harvard campus.
Days 5 -7: Boston, Massachusetts to Bar Harbor, Maine
The drive itself was stunning, with a couple of can’t miss stops along the way. Maine is the pinnacle of autumn beauty. We stayed outside of Bar Harbor to save on cost but the drive was absolutely worth it. The view from our Airbnb was perfection.
Where to stop along the way:
Salem, Massachusetts - Do a quick walking tour, or wander the town yourself!
Freeport, Maine - LL Bean Flagship Store - The store was absolutely massive and you can’t miss the photo opp with the giant LL Bean boot out front! Well worth the quick stop and there’s plenty of other shopping and dining in town too
Brickyard Hollow Brewing Company - The pizza and beer here was just what we needed before taking on the LL Bean stores.
Where to Stay
Ivy Manor Inn - If you’re staying in Bar Harbor, this place is an idyllic spot, right in the heart of town.
Waterfront Deer Isle Apartment w/ Fire Pit - Deer Isle is about 45 minutes away from Bar Harbor, but the drive is beautiful and this place was so beautiful we didn’t want to leave!
Where to Eat
Bar Harbor
Try Melt - Plenty of options if a lobster rolls aren’t for you
Ivy Manor Inn - Garden Bar - Grab a drink outside and enjoy live music after wandering around town
Deer Isle
Fin and Fern - If you’re staying outside of Bar Harbor and closer to Deer Isle (where we stayed), then this place was very cozy with great seafood options
44 North Coffee - Wonderful coffee spot with great pastries. Be warned, NO lattes.
What to Do:
Walk around Bar Harbor, there are so many cute shops and restaurants to explore, not to mention the view of the harbor.
Go for a hike in Acadia National Park - This is one of the most beautiful national parks in the country, therefore, parking is sparse. Get there early!