East Coast Fall Foliage Road Trip

East Coast Fall Foliage Road Trip

The Points Plan
A beautiful time of year to explore the East Coast.
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Itinerary

STL to Pittsburgh

If you're making your way to the East Coast from the Midwest, Pittsburgh is a great spot to stop for the night. 

STL to Pittsburgh - 9.5 hours

Dinner + Breakfast in Pittsburgh

Fairfield Inn & Suites Pittsburgh Downtown
@thepointsplan
In the heart of Downtown Pittsburgh. Conveniently located with valet parking
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Dinner Options

Bae Bae's Kitchen
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Quick and delicious Korean-inspired food. Not only is the restaurant interior cheerful and inviting, but their ingredients are organic and locally-sourced.
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Con Alma
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Live jazz featuring local musicians accompanies some of the best food and drinks in the city with a Latin-inspired menu paired with prohibition era classic cocktails.
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Nicky's Thai Kitchen
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Best Thai food in town. They have a lengthy menu to fit all tastes, and you can typically find dinner specials on their website. Plus, customers can choose between the bar or BYOB.
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Things to do

Fort Duquesne
@thepointsplan
Wonderful park that was easily walkable from the hotel.
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Pittsburgh to Catskills, New York

Take highway 28 (towards Phoenicia) for pretty scenic views

Hotel Vienna
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This perfect for a quick nights stay. A renovated motel that is clean and nicely finished. The rooms were very spacious and were dog friendly. Direct access to the Windham trail, which was wonderful to go for a quick walk after a long day of driving.
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Brandywine
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Old Italian restaurant with the best homemade, from scratch daily marinara sauce we've had this side of Italy.
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Zack's Place
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Great local's bar with the friendliest people. Zack's your bartender and head chef.
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Catskills to Boston

Mayflower Inn & Spa, Auberge Resorts Collection
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The Innspiration for the much loved Gilmore Girls TV Series. This is a stunningly beautiful, and very high-end Inn tuck away in Connecticut. Grab lunch and maybe a drink here and explore the pristine grounds.
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Sally's Apizza
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If you're looking for a spot to eat, this is it! Grab a pizza to go and eat at the park next door. There's even dedicated trash bins for pizza boxes only when you're done. The whole street is full of authentic Italian food.
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Moxy Boston Downtown
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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.
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Boston Food Stops:

Neptune Oyster
@thepointsplan
We waited an hour to get into this tiny restaurant that doesn't take reservations, but it was so worth it. Incredibly fresh and delicious seafood. We got oysters, johnny cake, scallops and a lobster roll and everything was the best we've ever had. This was expensive, but an unbeatable culinary experience.
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Union Oyster House
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The oldest restaurant with in-continuous service in the US. enjoy the fun history that covers the walls and order the scallops.
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What to Do

Freedom Trail Starting Point
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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.
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Public Garden
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Swan boats, and Good Will Hunting bench
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Boston Common
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Explore the beautiful park. Take a guided tour and learn some extra history.
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Charles River Esplanade
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Long trail the runs along the river. Its a beautiful place for a long walk or run. Also runs along Harvard campus
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 Boston to Bar Harbor, Maine

Stop in Salem to explore the town! 

Salem
@thepointsplan
1hr15min from Boston We didn't have the opportunity to stay long because there was absolutely no where to park due to an ongoing weekend festival.
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Brickyard Hollow Brewing Company
@thepointsplan
The pizza and beer was just what we needed before exploring all the LL Bean stores!
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Stop in Freeport, Maine at the L.L. Bean compound! There are at least 3 different stores and they are open 24/7!

L.L.Bean
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Multiple stores all LL Bean and I wasn't disappointed. Huge selection of clothes and gear.
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Deer Isle - Main Rental
@thepointsplan
We LOVED this place. Tucked away on little Deer Isle, a cozy and peaceful apartment with an incredible view over the water. On clear nights, you can see the stars through the skylight over the main bed. We were so comfortable here we didn't want to leave! Contact: info@thepointsplan to book!
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Fin and Fern
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Cozy restaurant with great seafood options.
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44 North Coffee - Stonington Café
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Wonderful coffee spot with great pastries. No lattes!
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Acadia National Park
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Truly one of the most beautiful National Parks we've visited. Make sure you get there early! Parking is limited
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Looking for More? Bar Harbor to Toronto

Staybridge Suites Niagara-on-the-Lake, an IHG Hotel
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Niagara Falls
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Queen Street
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Queen's Royal Park
@thepointsplan
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Pillitteri Estates Winery
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ABOUT THE AUTHOR
The Points Plan
We are an independent travel company that can help you fly to your dream destinations for practically free using points & miles AND I am also a certified travel advisor so that I can help you make the absolute most out of your next trip! Finding good places takes time and plenty of research, especially if you're trying to bring your family, friends and even your dog with you. We've done the research on where to stay, eat, and do with and sometimes without your dog so that you don't have to! We spent a year traveling all over Europe with our good boy, Copper, the dog (although he doesn't think he's *just* a dog). We've got places and activities that are dog-friendly as well as a few places where it's best to leave your furry friends at home. We have also planned romantic getaways, honeymoons, and friends trips all over the world. Oh hey, while you're here... We can also help get you to your dream destinations for (almost) free! We started The Points Plan to help other travelers book flights for (almost) free by developing custom travel rewards plans. We've traveled all over the world using our points and miles, and we want to fly you too! Did I mention I'm also a certified travel advisor? Once I fly you to your dream destination I want to help you find the perfect accommodations, restaurants, tours, and activities, all at no extra cost to you! (Seriously, the same price you would have found online). Let me put my Type A personality to work for you and help you on your next trip!
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