The cutest towns you need to visit on your 4 day road trip in New England, USA

Learn where to find the most adorable towns on your next road trip, that will make you fall in love with New England.


It has become our tradition to pack up our backpacks and hit the road every 4th of July weekend. We might not be able to travel across the country, climb the mountains or bungee jump from the tallest bridge, but we surely make the most of the 4 days we proudly own.

This year we ventured out further and covered over 900 miles (close to 1500 km) across plenty of picturesque towns, parks and breathtaking scenery. Which turned our weekend in the one of the most exciting road trips thus far.

DAY 1.  Massachusetts & Vermont

 Shelburne Falls, Massachusetts

Being such an accidental but yet fascinating discovery, The Flower Bridge, makes the top of this list. It is truly a landmark of this small quint town, with population of 1700 people, a very few restaurants and many friendly faces. It didn’t take long to walk the entire town and, of course, all road lead to the bridge of Flowers. Shelburne Falls resembles a medieval European city from a fairy tale and gives you a new prospective of hidden treasures of North East.

Brattleboro, Vermont

A cute town with a riverside gem, called The Marina Restaurant, that can turn your pit stop into a fun and scenic “lunching” experience. The restaurant sits at the meeting point of two states, New Hampshire and Vermont and lets you enjoy the peaceful scenery of both states.


The Green Mountains, Vermont

A hidden gem where you will find yourself alone in entire park (well, that’s an overstatement but it tends to be less busy than any other national park I have visited). The trails are great,  picturesque with minimal ascent or descent that lead to a waterfall.


Woodstock, Vermont

Woodstock, VT is one charming town in New England (there is a Woodstock in every state). It’s an adorable walkable town, with very “American” feel to it. Bridges and street lanterns with flower pots, Flannel shops, cute houses with picket fences, American flags on every corner all make it one of my favorite towns in the North East.

My fav – Ice Cream Creamery is well-known in the neighborhood for its delicious ice cream selection.


DAY 2. New Hampshire

Kancamagus highway, New Hamphire (Route 112)

Is a well-known among New Englanders highway that runs for over 56mi (90 km) across White Mountain National Forest. The drive is magnificent on its own that passes lush forests, mountains, gorges and rivers.


Franconia notch state park and Flume gorge, New Hampshire

Located off of Tripoli Highway, a less impressive version of Kancamagus highway, that leads to the Flume Gorge. You can count on a short and easy hike that takes you on a dramatic walk through the gorge. The park can be crowded in a busy season, so come early. Regardless of the time of the day, it still radiates serenity and the views of the waterfalls are spectacular.

Day 3. New Hamphire & Maine

Portsmouth, New Hampshire

Portsmouth is worth a quick stop and walk around. Being another cute town, it has a large young generation presence with lots of bars and hang out spots. Thus count to spend some time there to bar hop.

Great bar – Ri Ri bar is an old failed bank turned into a bar- great outdoor seating for people-watching


Portland, Maine 

Is a true sea-port beautiful old town with cobble stone roads, old buildings, fishing boats, cruises and sea food goodies everywhere you look. That’s where you will find countless bars that serve fresh out of the ocean lobsters and, mind you, it’s a crime not to try one while in Maine. For cheap!

Old Port Tavern is a fantastic bar with a spectacular design and a huge fish tank. The food is out of this world, so be sure you get their special with two HUGE lobsters for $24.00USD or less.

The north point bar is a great laid back bar with alluring happy hour and attentive customer service.


Day 4. Rhode Island

Newport, Rhode Island

Is a true New England town and a coastal beauty that has it all: elegance, history, culture, and food. Downtown is relatively small with cute boutique shops and galleries, inviting restaurants, great sea food and desert shops.  Not to mention, only within a 5 minute drive you can visit the famous Newport Mansions. The old mansions that once belonged to prosperous privileged families whose names are among the history books, like the Vanderbilts, are now turned into museums.

The lodging in New Port can be quite expensive, particularly during holidays and festivals. If you try to overnight a few miles outside of New Port, you could find a bargain on accommodation. Needless to say, you will get to see the surroundings of one of the wealthiest towns in USA.


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