Hi, I’m Hannah - Product Manager at Guess Where Trips.
Winter road trips in the Northeast have a charm all their own. From small towns to scenic viewpoints, winter brings a cozy, more intimate feel to places you might overlook the rest of the year.
In this post, I'm sharing my top favourite winter road trips across the Northeast USA including my top winter road trip tips and recommended winter accommodations.
Take a look at the map below to get a general idea of where these winter road trips end.
My Favourite Winter Trips in the Northeast...
Taking this trip in the winter? Here are my tips for 'Winding Roads & Historic Gems':
- Important note: This is a fabulous winter trip, and we especially recommend travelling on a Friday or Saturday in the winter months. Note that one featured farm option on stop #1 is closed in the winter, but we provide year-round alternatives!
- Bring your winter gear: Be sure to wear good boots or bring your snowshoes, as we've got tons of great winter trail options on this trip!
- A cozy must-stop: You've got to visit our corner store suggestion on stop #2 - it is truly the coziest place ever!
- A warm winter pause: With amazing views and a cozy fireplace, our winery suggestion on stop #3 is the perfect winter stop.
- Depart after mid-January: Note that our 4th stop town is beautiful in the wintertime, but a many of the shops/eateries are closed for the first half of January! We recommend visiting after mid-January.
- Cozy through and through: This cute coffee shop & marketplace has come of the best coffee in town plus a cozy wood-burning fireplace!
- Let loose in the snow: Enjoy fun winter tubing, great for kids and adults alike!
- Hit the ice: Grab your skates and enjoy some winter ice skating! They also have skate rentals; reservations not needed but recommended for weekends.
Recommended Winter Stays for 'Winding Roads & Historic Gems'
Luxe & Picturesque Dome Haven
Silo Cabin-Harpers Ferry Nature!
Taking this trip in the winter? Here are my tips for 'Charming Curiosities':
- Make a reservation on stop 1: Our sit-down breakfast option on stop #1 can get busy on weekends, but we promise it is worth the wait! If it's busy, put your name on their waitlist, then go wander the cute town until your table is ready.
- Bring your winter gear: Be sure to wear good winter boots to explore our two outdoor options on stop #2!
- A cozy reward: Warm up after your outdoor adventures inside a heated wine tent at our featured winery on stop #3! Advance reservations are required, so this one is worth peeking at and booking early!
- Straight out of a movie: Our small town suggestion for stop #4 is Hallmark-worthy and will help you feel all the cozy winter vibes.
- Sip something special: Lovers of whiskey and bourbon will enjoy a tour and tasting at Virginia's oldest and most award-winning distillery, near our 4th stop!
- Keep the fun going: Year-round ice skating at this fun wilderness resort just 25 minutes from our final stop.
- Pack your toboggans for this detour: Bringing kids along? Be sure to pack your toboggans as there are tons of great sledding hills nearby that could make for a whole day of winter fun!
Recommended Winter Stays for 'Charming Curiosities'
Holiday Little Stone Mill Historic Fredericksburg
Ironclad Inn
Taking this trip in the winter? Here are my tips for 'Covered Bridges & Baked Goods'
- Bring your cameras: you'll want to take pictures of our 6 beautiful covered bridges on stops #1 and #2. You'll be sure to fill your entire camera roll when these picturesque bridges are covered in snow.
- Plan ahead for this one: If you're lucky, there might be a tour of our stop #3 bakery suggestion while you're there. We highly recommend getting on a tour if you can, or plan to come back in the future. Take a peek here if you want to pre-reserve your spot on a tour!
- Important note: Note that some of our suggestions on stop #4 close around 4pm or 5pm, so be sure to plan your time accordingly. Or, if this is an overnight getaway, you can always check out our stop #4 options the next day!
- Don't miss the Fire & Ice festival: Our 3rd stop town has an annual Fire & Ice festival for 10 days in February. This is a fabulous time to travel and make the most of this cool event!
- Visit a nearby wolf sanctuary for a truly unique winter activity: Public or private tours available; they do sell out so plan ahead as new availability opens on the 1st of each month.
- A winter thrill: Winter ziplining is probably something you've never experienced, but it's so worth it to get a bird's eye view of the snowy treetops! Just be sure to bundle up on super chilly days!
Recommended Winter Stays for 'Covered Bridges & Baked Goods'
Cozy Cottage (Air bnb)
The Barn on Fox Alley
Taking this trip in the winter? Here are my tips for 'Hudson River Hideaways'
- Be winter-ready: Wear good boots to enjoy our walking trails during snowy weather. If you have snowshoes, definitely bring them along as there are some great snowshoeing options too.
- Gear up for stop 2: Our featured suggestion on stop #2 is a fantastic spot for cross-country skiing and sledding, so bring your winter gear!
- A post-hike treat: Warm up with a tasty seasonal latte at our suggested coffeehouse on stop #3, perfect post-hike.
- Warm up with a pint: Both of our featured breweries on stop #4 have cozy taprooms to get away from the winter chill and warm up with a pint.
- An easy winter add-on: This fun winter park is just 15 minutes from stop #3 and has sledding, skiing, & snowshoeing (plus rentals if you don't have your own gear).
- Want to go on another hike?: Amazing winter hikes await at this state park that is between stops #3 and #4 on your trip.
- Dinner with a view: This riverside restaurant near stop #1 has igloo dining with river views! A perfect spot to come back to for dinner or save for a future day trip - reserve in advance!
Recommended Winter Stays for 'Hudson River Hideaways'
The Treehouse Lovenest
Viridian House
Taking this trip in the winter? Here are my tips for 'Funky Farms & Storybook Tales'
- Don't forget your winter gear: Our featured suggestion on stop #1 has snowshoeing and cross-country skiing trails in the snowy months, so be sure to bring your winter gear along.
- Important note: Our featured farm on stop #2 is seasonal and isn't open until July; however, we've provided an optional wildlife refuge that is fabulous for winter hikes plus an eatery where you can warm-up post-hike.
- Plan ahead for the final stop: The final stop is in a cozy winter town that totally gives off Hallmark vibes, with tons of great spots to head inside and warm up. Note that our featured house is still open for tours; however, it closes earlier in the winter time, so be sure to plan your day accordingly or book a tour for the following day.
- Dress for the season: Be sure to bundle up so you can enjoy our featured farm on stop #3! It's lovely for winter strolls and learning about how farm animals survive the coldest months.
- A cozy meal stop: Have breakfast or lunch in this historic train depot, the perfect winter warm-up spot!
- An easy final add-on: Just 10 minutes from your final stop you'll find this beautiful outdoor sculpture park that is open year-round. Perfect for snowy winter strolls.
- Travel Jan 23-24, 2026: to experience the Winter Fest that happens in our 4th stop town.
Recommended Winter Stays for 'Funky Farms & Storybook Tales'
The Abbey Inn & Spa
Concord’s Colonial Inn
Author: Hannah Elias
Hannah is the Product Manager at Guess Where Trips. From product launch strategy to research & development (and even writing our Detour Diaries book!), she continues to find new ways to improve our road trip products for customers.
