New Hampshire: Must-Sees

If I wasn’t living in a vibrant, bustling city by the time I was eighteen, my life amounted to nothing. This was my teenage mantra and one I firmly upheld until I chose to go to a university that had significantly less streets than my hometown… and had to explain that decision to the people who had heard my city speech. Beneath the layers of stubbornness, I had come to appreciate living in my home state where small town charm thrives and a wide variety of travel urges can all be satisfied in a weekend.

Although most first time New England tourists focus on Boston, these four New Hampshire towns are worth at least a weekend of your trip. Portsmouth is accessible from Boston by bus or train but there’s a reason why people backpack around Europe and road trip around America. These towns are best explored by car.


For nine years in a row, Wolfeboro was my summer playground. The town itself is just a road’s length but you’re better off kayaking, sailing, or water skiing around Lake Winnipesaukee anyway. The Wolfeboro Inn is a popular place to stay but for a longer and secluded retreat, many vacation rentals available are homier and situated closer to the lakeside. The food is more comforting than gourmet but don’t let that stop you from trying the Yum Yum shop’s pizza or treats from Crepes Ooh La La!

The Castle in the Clouds, located just a 20 minute drive up the road has a plethora of hiking trails. The Castle delivers a great view of the surrounding nature and you can also meet the largest horse in the world, Zeus. The 3000lb horse isn’t part of the horseback riding deal, but you can ride Napoleon, Scarlett, or Scooter!


Jackson NH encompasses all that is wonderful about the four seasons in New Hampshire. The drive on the Mount Washington Auto Road leads up to New England’s highest peak and is a perfect way to soak up the famous ‘fall foliage’. During the winter, there are ample opportunities for snowmobiling and skiing around Black Mountain. Classic New England charm abounds at the “Honeymoon Bridge” – worth at least pulling over on Route 16 for a photo. Also, if at any point along the highway, you see a house-sized shoe or an anthropomorphized egg, it’s not a hallucination. You just passed one of New Hampshire’s popular parks, Storyland.

If you’re around the White Mountains region during the summer, the Lost River Gorge is about an hour’s drive away but a good excursion for some easy trails. But… can you conquer the Lemon Squeeze? 

 Rye/New Castle

Nestled next to Portsmouth, this small town cluster makes the list for its beaches and famous hotel, Wentworth by the Sea. Wallis Sands or Jenness Beach in Rye are quieter and classier alternatives to nearby Hampton (Skankton) Beach. The Newcastle Commons are also a popular picnicking stop and the explorer can look for the hidden beaches adjacent to the park.

If you’re looking to splurge, take advantage of a night at the Wentworth, a majestic hotel that reopened its doors in 2003. If not, it’s still worth a drive down to look around the docks or go sailing. Portsmouth offers too many culinary delights to pass up but on the way home, pick up an ice cream from the Ice House.


No New Hampshire trip is complete without a day in Portsmouth. Portsmouth has the miraculous ability to successfully and simultaneously cater to families, retirees, and college students. It is also the most accessible town on the list from Boston. For history buffs, a summer day is well spent walking around Strawberry Banke and neighboring Prescott Park. Plays are always on during the summer. If you’re lucky enough to be there over Christmas break, The Player’s Ring, a ‘hole in the wall’ theater within the park, does a marvelous version of A Christmas Carol.

Most local students, myself included, spend an obscene amount of time and money at Breaking New Grounds, a local chain coffee shop. Don’t be swayed by the Starbucks across the street, this coffee is worth a try. Its prime location and outdoor seating give you a front row seat to observe the characters of Portsmouth. For dinner, Cava, a Tapas Bar down Commercial Alley or Flatbreads are my top picks!


If none of this has enticed you, the tax-free shopping should! New Hampshire is definitely an underrated state in New England but a car and a willingness to get lost will give you a truly authentic New England visit. 


Images sourced from Rhiann MacKenzieMark ZacksJames Walsh, Michael L. Baird, and Anne Hodges.