Romantic Valentine’s Day Road Trip Ideas

valentine's day road trip ideas in the northeast


Valentine’s Day is approaching!  This annual celebration of love is usually accompanied by the pressure to impress your date.  But this year, we’ve got you covered.  Why not take a romantic Valentine’s Day road trip?  We’ve compiled a list of romantic places to visit this Valentine’s Day.  In no particular order, here are some road trip ideas for your February 14th:


1. Woodstock, VT

Coined “the prettiest small town in America”, Woodstock as all the appeal of a romantic getaway.  Beautiful untouched views, a cute and classic main street, and small town attractions, you and your Valentine will surely have a good time.  Woodstock also boasts resorts and inn for all your pampering desires.

Approximate Travel Time:

2 Hours from our MA office
3.5 Hours from CT
6.5 Hours from NJ

Our Picks

Valentine’s Reservation:  Stay at the romantic Jackson House Inn – a cozy and warm for you and your Valentine.  Head out to Cloudland Farm Restaurant for an upscale, country-style dining experience.

Romantic Activity: Make a stop at Sugarbush Farm.  They have homemade maple syrup and cheese tasting.  The farm is also flaunts a beautiful winter landscape for you and your date to explore.


2. Boston, MA

Boston is a perfect backdrop for a romantic getaway.  It’s rich with history but holds a vibrant aura.  You and your Valentine will have an array of activities to partake in.  Whatever your interests are, there is something to accommodate them.  And, brownstone buildings will serve as a great background for photos!

Approximate Travel Time: 

2 hours from our MA office
2.5 hours from CT
4.5 hours from NJ

Our Picks

Valentine’s Reservation: Head to Carmen tucked away in Boston’s North End. Enjoy a romantic meal by candlelight and head to Modern Pastry after for dessert. You’ll want to make a reservation – this intimate restaurant only has a few tables!

Romantic Activity: Stroll along Boston’s famed Newbury Street, then pop into MET Back Bay for their “Hot Chocolate Experience,” we’re you and your love can taste 4 different, decked out hot chocolates!


3. Cape Cod, MA

Cape Cod is known for their summers and beaches, but now is the perfect time to visit.  The off season means cheaper accommodation and you can experience the sights without crowds of people.  Provincetown is a must-see if you are on the Cape – it’s an eclectic collection of all people.

Approximate Travel Time:

2.5 hours from our MA office
3 hours from CT
5.5 hours from NJ

Our Picks

Valentine’s Reservation: Book a dinner meal at the Red Inn in Provincetown.  It’s a quaint restaurant with wonderful food and a view of the water.  It does get crowded, so make sure to plan ahead.

Romantic Activity: Visit Commercial Street in Provincetown for an abundance and shopping and be sure to wander down to Racepoint Beach and watch the sunset.


4. Montreal, QC, Canada

While Montreal is beyond the boarder of the United States, this Canadian city is just a drive away.  Quebec holds strong French influences.  From the language to the architecture to the food, there’s no shortage of European flair.  There are also plenty of things to do – skiing, shopping, sightseeing and more.  The best part?  Montreal has an underground mall so you don’t need to venture into the cold if you don’t want to.

Approximate Travel Time:

4.5 Hours from our MA office
5.5 Hours from CT
7 Hours from NJ

Our Picks

Valentine’s Reservation: For a chic dining experience, get a reservation for you and your date at le Serpent Resturant or Salmigondis.

Romantic Activity: Get a spa pampering at Bota Bota.  Or for something more physical, do outdoor ice skating at the Parc Lafontaine.  Camellia Sinensis Tea House offers tea tasting lessons that you and your date could try.


5. New York, NY

New York is one of the world’s greatest hubs for music, culture, fashion, and food.  In NY, you and your Valentine will never run out of things to do.  Whether you see a show on Broadway, stroll through Central Park, or just hang out, you’ll never be bored.

Approximate Travel Time:

3 Hours from our MA office
2 Hours from CT
3 Hours from NJ

Our Picks

Valentine’s Reservation: Le Berdanin is one of New York top seafood restaurant with a high price tag.  We also recommend Casa Mono for you and your Valentine.  After dinner, you should head to Momofuku Milk bar for their cereal milk ice cream.

Romantic Activity: Grab an upscale brunch at Cookshop (you may need to make a reservation!) and afterwards take a romantic walk around the highline for some of the best views of the city!  If you get cold, pick up some world famous hot chocolate from Max Brenner.


6. Lake George, NY

Lake George is brimming with rich history and beautiful landscapes.  For those interested in history, there are tours and sites to poke around.  There are also fun activities that you and your loved one can enjoy together, such as wine tasting!  There are plenty of nature-related activities worth your time, if you can brave the cold! Staying in and enjoying the luxuries of a resort is an option as well.

Approximate Travel Time:

3 Hours from our MA office
3 Hours from CT
5 Hours from NJ

Our Picks

Valentine’s Reservation: Have a romantic weekend at The Inn at Erlowest.  The Bedand Breakfast is elegant and stylish.  We also recommend eating in their restaurant for a Valentine’s Day Dinner.

Romantic Activity: You and your date can do some wine tasting at Adirondack Winery!  They are hosting a special Valentine’s Day event so make sure to book your spot beforehand. There’s also an annual winter carnival to check out.  And make sure to enjoy the Lake itself.


7. Burlington, VT

This Northern city has all the romantic winter experiences that you and your date need.  With some of the best skiing on the East Coast, you’ll be on the mountain all day.  There is also downtown Burlington with shopping, dining and nightlife.  After a long day, you can keep cozy in a lodge or inn.

Approximate Travel Time:

3.5 Hours from MA
5 Hours from CT
7 Hours from NJ

Our Picks

Valentine’s Reservation: We recommend making a reservation at Delia’s Trattoria.  It’s a small restaurant with a cozy atmosphere, which is perfect for a romantic dinner.  When in Burlington, it’s almost a requirement to get Ben and Jerry’s Ice cream after dinner.

Romantic Activity: Burlington’s Church Street makes for a great stroll around.  You can also check out a show at Flynn Center for the performing arts.  Or, if the arts are not your cup of tea, Switchback Brewing Company offers tours of their brewery on Saturdays!


8. Alexandria, VA

Trying to escape the bitter cold of the North?  Alexandria, VA is a fantastic place to get away.  This city is outside of Washington, DC and has the charm of a small town.  Alexandria is also extremely dog friendly, so if you can’t bear to be separated from your pooch, they’ll be more than welcome.  This town is romantic enough for a Valentine’s Day – The Obama’s have visited Alexandria for their anniversary!

Approximate Travel Time:

7 Hours from our MA office
6 Hours from CT
4 Hours from NJ

Our Picks

Valentine’s Reservation: The Jackson 20 restaurant will make for a memorable Valentine’s Day dinner.  It has Southern charm without being overbearing.

Romantic Activity: Old Town Alexandria is the highlight of this small city.  With old Southern influence, you and your date can wander through the streets.  Stop and grab a coffee or a snack on your way around the area.  It makes for a great romantic afternoon.


9. Portsmouth, NH

If you want to take your loved one somewhere quieter this Valentine’s Day, consider Portsmouth, NH.  Located on the water, Portsmouth offers visitors an abundance to see and do.  Tour Strawbery Banke, a living museum.   While the Historic Houses may not be open in the winter, you are free to wander through the grounds or visit the indoor museum portion.  Portsmouth’s shopping and dining are located along the water, which makes for an ideal romantic meal.

Approximate Travel Time:

2.5 Hours from our MA office
3.5 Hours from CT
6 Hours from NJ

Our Picks

Valentine’s Reservation: Have a romantic French dinner at Bridge Street Bistro & Wine Bar.  With a variety of wines and authentic French cuisines, it’s the perfect way to begin a romantic evening.

Romantic Activity:  We recommend that you and your Valentine visit Strawbery Banke and have a walk around the grounds.  The Market Square, which is the downtown area, is another option for enjoy a romantic day with your date.


10. Portland, ME

This coastal city has a classic New England feel.  Portland is a mix of old and new, artsy and outdoorsy, and down-to-Earth and sophisticated.  With a widespread variety of things to do, Portland is an exceptional destination for all couples.  Seafood, art, shopping, and more are all accessible to those who decide to visit.

Approximate Travel Time:

3 Hours from our MA office
4 Hours from CT
7 Hours from NJ

Our Picks

Valentine’s Reservation: Have your romantic dinner at Paciarino.  You cannot go wrong with homemade pasta and wine.

Romantic Activity: Take a tour of Victoria Mansion with your Valentine and relish in the ornate décor.  Or take a brewery tour of Allagash Brewery.  Commercial Street is a shopping and dining hub where you and your date can explore.


When going on a road trip, especially in the winter, make sure that your car is prepared to handle the drive.  Get your car checked prior to departure, and put essential items inside in case you accidentally get caught in a storm. You can check out our Winter Insurance Guide for a helpful checklist.

Be sure that your car insurance will cover you if something were to happen on your trip.  You wouldn’t want that to ruin your Valentine’s Day getaway!
Happy Valentine’s Day from Encharter!

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