Ready for the ultimate New England fall road trip? Picture this: 4 nights at cozy, handpicked HelmsBnB homes, each nestled in a scenic destination where vibrant foliage meets charming small-town vibes. This curated journey takes you from the streets of historic Salem to the mountain views of Killington, with two exciting stops every day to explore. With multiple properties available across Massachusetts, Maine, New Hampshire, and Vermont, you can choose the perfect HelmsBnB homes for your ideal fall getaway and group size. Since all of our rentals are managed under the same team, you’ll enjoy a seamless experience from one stop to the next.
We’ve mapped out a route for you, but click our Google Maps link to adjust and customize your adventure with the rentals and stops of your choice. At the end of the guide, you'll find ticket links for key attractions and food recommendations along your route. Feel free to reach out to our team for personalized booking recommendations, tips for your journey, or any questions you may have!
Bonus: If you book 2 or more locations with us, we offer an exclusive 15% discount. Reach out to use this!
THE ROAD TRIP ITINERARY:
NIGHT 1: Land in Boston — Stay at Medford, MA HelmsBnB
DAY 1:
Leave: Medford, MA
Breakfast at Cafe del Mar/Gas
Stop 1: Salem, MA (Morning) – 25 min drive
Time to explore: ~3 hours
Stop 2: Kennebunk, ME (Afternoon) – 1 hour 15 min drive
Time to explore: ~2.5 hour (enjoy dinner here)
Arrive: Bath, ME – 1 hour drive
Arrive around 7 PM
NIGHT 2: Stay at Bath, ME HelmsBnB
DAY 2 :
Leave: Bath, ME
Breakfast at the infamous Mae’s Cafe
Stop 1: Conway Scenic Railroad – 2 hour drive
Time to explore: ~ 2 hours (purchase tickets in advance)
Stop 2: Santa’s Village – 1 hour drive
Time to explore: ~ 2.5 hours (purchase tickets in advance)
Arrive: Jefferson, NH Home – 10 min drive
Time to settle in: Enjoy the hot tub & s'mores by the fire
NIGHT 3: Stay at Jefferson, NH HelmsBnB
DAY 3:
Leave: Jefferson, NH
Stop 1: Franconia Notch State Park – 40 min drive
Time to explore: ~ ½ hour (Scenic photos)
Arrive: Woodstock, VT – 1 hour 15 min drive
Time to settle in and enjoy their famous afternoon snacks: ~1 hour
Visit: Killington Mtn Gondola – 15 min drive
Time to explore: ~2.5 hours (purchase tickets in advance)
Head back: Woodstock, VT – 15 min drive
Grab pizza at Ramunto’s and enjoy game night
NIGHT 4: Stay at Woodstock, VT HelmsBnB
DAY 5:
Leave: Woodstock, VT
Breakfast at the Woodbridge Inn that will fuel you for your whole day of exploring
Stop: Smolak Farms, North Andover, MA – 1 hour 45 min drive
Time to explore: ~2 hours (Enjoy bakery, lunch, and kids’ playground)
Arrive: Boston Logan for evening flight – 45 min drive
Arrive by 4 PM for an evening flight
DESTINATION DETAILS & LINKS:
As you journey along your fall road trip, here’s a look at some top spots to explore, with ticket links and local food recommendations to keep your adventure fueled.
Salem, MA–
Attractions:
Salem Witch Museum – Explore the history of the Salem witch trials through exhibits and reenactments.
Ticket Link: Salem Witch Museum Tickets
The House of the Seven Gables – This historic mansion offers tours showcasing the home’s history and its connection to Nathaniel Hawthorne.
Ticket Link: The House of the Seven Gables Tickets
Salem Common – A perfect spot to relax and enjoy the atmosphere of Salem’s historic district.
Food Recommendations:
Red's Sandwich Shop – A beloved local spot known for hearty breakfast and lunch options, such as their famous lobster rolls.
Turner’s Seafood – An excellent choice for fresh seafood, including clam chowder and lobster dishes, located right on Derby Wharf.
BrewBox – For a laid-back experience, BrewBox offers craft beer and pizza, located conveniently in the heart of Salem.
Kennebunkport, ME–
Attractions:
Rachel Carson National Wildlife Refuge – A beautiful nature preserve ideal for bird watching and nature walks.
Ticket Link: Rachel Carson Refuge Info
Kennebunkport Walks – Explore this charming town through guided walking tours that cover history, architecture, and local tales.
Ticket Link: Kennebunkport Walks Tickets
Food Recommendations:
Mabel’s Lobster Claw – A cozy spot offering New England seafood classics like lobster rolls and clam chowder.
The Clam Shack – Famous for its fried clams and lobster rolls, this casual spot is a must-try for seafood lovers.
Old Vines Wine Bar – A relaxed place to enjoy wine pairings with Mediterranean-inspired dishes.
The Boathouse – Offering fresh seafood and cocktails right on the water, this restaurant boasts a lively, laid-back atmosphere perfect for enjoying the coastal vibe of Kennebunkport.
Conway Scenic Railroad (Conway, NH)–
Attractions:
Conway Scenic Railroad – Hop aboard a historic train for a scenic ride through the White Mountains. The Notch Train and Mountaineer routes offer stunning views, and both are under 2 hours of travel.
Ticket Link: Conway Scenic Railroad Tickets
Ticket Info: The Notch Train (1.5 hours) and Mountaineer (1 hour 45 minutes) are ideal for a scenic, short journey. Be sure to book in advance, especially in fall for peak foliage season.
Food Recommendations (Nearby):
The Moat Mountain Smokehouse & Brewing Co. – A great spot for BBQ and craft beer, located in Conway, ideal for a casual meal before or after the train ride.
Vito Marcello’s Italian Bistro – Cozy Italian fare, perfect for a sit-down meal in the charming town of Conway.
Santa’s Village (Jefferson, NH)–
Attractions:
Santa’s Village – A Christmas-themed amusement park that offers fun for all ages, featuring rides, games, and a chance to meet Santa!
Ticket Link: Santa’s Village Tickets
Ticket Info: Be sure to purchase tickets in advance for the best experience. Check for any seasonal discounts.
Food Recommendations:
Santa’s Village Dining – The park has a variety of quick-service dining options like burgers, fries, and themed treats. There are also picnic areas where you can bring your own food.
The Bethlehem Country Store – Grab a delicious homemade meal or snack while shopping for local goods.
Franconia Notch State Park (Franconia, NH):
Attractions:
Franconia Notch State Park – A scenic park with incredible views, perfect for a quick stop to stretch your legs and capture some breathtaking photos. The park is home to The Flume Gorge and Echo Lake, both of which are ideal for a short hike or a photo op.
Ticket Info: Tickets for the Flume Gorge are available at the park entrance. A short hike is required for viewing the gorge.
Food Recommendations (Nearby):
The Pollyanna of Littleton – A charming cafe with great coffee, sandwiches, and pastries. Located just outside Franconia, this is perfect for a break.
Fresolone’s Pizza Pasta & Sub – A family-friendly spot for classic Italian meals, pizza, and subs.
Woodstock/Killington, VT:
Attractions:
Killington Mountain Gondola – Take the scenic gondola ride for stunning views of the surrounding mountains. Whether you want to hike or simply enjoy the views, this is a perfect stop.
Ticket Link: Killington Mountain Gondola Tickets
Ticket Info: Purchase tickets for the gondola ride directly on the Killington Resort website. It's best to check for any fall-specific hours and pricing.
Food Recommendations:
Ramuntos Brick & Brew Pizza – Great Food, Great People! Conveniently located on Route 4 between Woodstock & Killington, Vermont.
Au Comptoir: A cozy French bistro in Woodstock offering authentic Parisian fare with a modern twist, perfect for a romantic dinner or brunch.
Mon Vert Cafe: A farm-to-table café in Woodstock serving fresh, local dishes in a casual, inviting atmosphere, ideal for brunch or lunch.
The Foundry at Summit Pond – A beautiful restaurant with a scenic view of Summit Pond, offering a variety of American dishes and craft beer.
Killington Diner – A classic, family-friendly spot for breakfast or lunch with hearty options like pancakes, waffles, and eggs.
Smolak Farms (North Andover, MA):
Attractions:
Smolak Farms – A family-friendly stop with a bakery, kids' playground, and the opportunity to pick your own apples during the fall season.
Ticket Info: No tickets required for general entry, but some activities (like apple picking or pumpkin patches) may have a small fee.
Website: Smolak Farms
Food Recommendations:
Smolak Farms Bakery – A delicious spot for fresh baked goods, cider donuts, and locally made jams. Grab a treat before continuing your journey.
The Grille at Smolak Farms – For a quick lunch, the Grille serves casual options like sandwiches and salads, ideal for a pit stop.
READY TO HIT THE ROAD?
This 5-day itinerary combines scenic drives, fantastic activities, and cozy stays that will make your fall road trip unforgettable. Don’t forget to book your spots directly with HelmsBnB for an effortless journey as soon as you touch down at Logan! Safe travels and enjoy the beauty of New England.
Contact: hello@helmsbnb.com
Search: helmsbnb.com/destinations
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