Fall In Love In Littleton New Hampshire

Women's Dating

Fall In Love On A Romantic Autumn Getaway To Littleton, New Hampshire

Lexi Inks

Written by: Lexi Inks

Lexi Inks

Lexi joined the DatingAdvice team with several years of lifestyle journalism experience. She grew her writing prowess through reporting on the topic of sex and relationships, and she loves continuing to cover content in this niche while working toward becoming an AASECT Certified Sexuality Educator. You can find Lexi's writing in Refinery29, Cosmopolitan, Bustle, Well + Good, and Women's Health, among other publications.

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Edited by: Lillian Castro

Lillian Castro

Lillian Guevara-Castro brings more than 30 years of journalism experience to ensure DatingAdvice articles have been edited for overall clarity, accuracy, and reader engagement. She has worked at The Atlanta Journal and Constitution, The Gwinnett Daily News, and The Gainesville Sun covering lifestyle topics.

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The Short Version: Breathtaking colors and cool breezes aren’t the only things to enjoy about the fall season — especially in a town like Littleton, New Hampshire. Nestled among the New England mountains and not far from large attractions like Boston and Burlington, Littleton is a small but lovely place to take a foliage-filled foray with your significant other. From its pumpkin carving festival to intimate date night eateries, you and your boo are sure to “fall” in love with Littleton.

When you’re planning trips with your partner, there are several things you may want to consider. If you live somewhere like Miami and you’re hoping to escape the heat and get somewhere a little cooler for a change, heading to Arizona during the summer may not provide much relief. Traveling with your significant other in the fall, however, might give you more options. 

The leaves changing color and the cool, crisp air are some of the major perks to vacationing during autumn. Especially for people like myself — a native Floridian still handling the South’s humidity — a visit to the northeastern United States sounds brilliant in those later months of the year. 

Littleton, New Hampshire aerial view of Fall
Littleton, NH is full of stunning colors during the fall months.

Those of us who live down yonder tend to miss out on walking through a path of crunchy, colorful leaves and enjoying October bonfires with friends. On the flip side, people living in the New England area enjoy all the benefits of this transitional time of year. Locals of towns like Littleton, New Hampshire, especially experience the beauty of fall and all the romance and nostalgia it has to offer. 

Littleton may have a small population of 6,043, but don’t let that fool you — this New England town is packed full of sights to see and things to do. Nestled in the White Mountains of New Hampshire, spokesperson Veronica Francis told us that Littleton is a great “crossover town” for those vacationing in larger nearby cities like Boston or Montreal. 

Aside from the mountain views and bountiful opportunities to get out and explore nature, Littleton also offers historic charm and friendly places and people. Whether you and your partner are passing through for an exciting city getaway or would rather find a low-key locale for a quiet retreat, little Littleton is certainly worth a visit. 

Seasonal Surprises Await

New England is one of the best areas to visit for fall travels. Countless movies and TV shows are set there, giving a special kind of nostalgia and wistfulness to the idea of taking a trip up to the Northeast. Mountain towns like Littleton offer a unique opportunity to bask in the beauty of fall and everything the season brings with it. 

Mountains in Littleton, New Hampshire
Snow-capped mountains nearby allow for plenty of seasonal sports in the fall and winter.

“We’re fortunate that we’re a four season destination,” Veronica said. “The fall is the most popular and the foliage brings people from around the world. We are right in the middle of some scenic routes where you can drive through, have lunch in Littleton, and then continue on and see the gorgeous colors. That’s usually September and October.”

When visiting Littleton, you and your partner can take part in fun fall activities like strolling through town to see the gorgeous trees or pumpkin carving at the town’s Gathering of the Jack O’Lanterns. A wonderful celebration of the spooky season, this gathering includes a spectacle of glowing carved pumpkins lining the river, a haunted riverwalk, and a family-friendly bonfire. 

The fall is undoubtedly one of the best times of year to visit Littleton, but Veronica shared that it isn’t the only time when the town really shines. 

“Christmas is a beautiful time. We light up the whole town and the downtown gets gorgeous holiday lights. The day after Thanksgiving we have a classic holiday parade that comes right down the main street, so you can watch an old fashioned parade that people like to come visit and do some nice holiday shopping or view the lights.”

Littleton, New Hampshire library with lit Christmas trees
The entire town is lit up with festive decor during the holiday season.

Once the snow begins to fall, Veronica said that ski season is all the rage in Littleton. The city is close to four major ski areas, and locals often enjoy downhill cross country skiing, snowshoeing, and snowmobiling, among other sports. Even if you aren’t the most athletic person but you still want to watch your partner shred the slopes, Veronica noted that Littleton is a fantastic place to stop in, gather some snow supplies and a warm cup of hot chocolate, then head out to the trails.

Summer, too, is a great time to swing through the small town. Once June hits, Veronica told us that there are plenty of sights to see and activities to take part in. For one, Littleton is known for its lupins — the state of New Hampshire’s gorgeous purple flower. She said that there are open fields full of them, and they are a great spot where you and your honeybee can take pictures and stroll along the scenic trails. 

River bridge in Littleton, New Hampshire
Taking a scenic walk along the river is a popular activity in the summertime.

For more adventurous folks, the bike shop in Littleton has gear rentals for mountain biking. If this applies to you and your significant other, Veronica recommends riding along the gravel path by the river for some sunny summer views, in addition to the mountain trails surrounding the town.

A Place for Quiet Romance 

As the leaves themselves fall, cuffing season often leaves people falling in love themselves. Meeting a new boo is customary before the holiday season, so taking advantage of the gorgeous sights and intimate date spots in New England towns like Littleton can provide a super romantic experience.

No matter if you’re newly cuffed or have been going steady for years, you and your special person can experience plenty of memorable moments together while staying in Littleton. Veronica said that the town is known for its locally made beers and spirits, including unique breweries in its downtown area. 

Once you and your partner have shared a toast or three to your love, there is more to explore. From casual eats to fine dining, Littleton has several great date night spots to choose from. 

Aerial view of downtown Littleton, New Hampshire
Littleton’s downtown area is full of fun shops and local eateries.

“We have the Beal House Inn that gets rave reviews. It’s a cozy restaurant where you can have a nice dinner,” Veronica shared. “Five minutes out is the Adair Inn, and they’re named one of the most romantic inns in New Hampshire. They have a beautiful dining room along with fireplace rooms. And they also have a bunch of trails around their properties, it’s a gorgeous property with views.”

She also shouted out two delicious Thai spots for those with an international palette. Both are award-winning Thai spots: Taste the Thai, and Chang Thai Cafe. Additionally, if you and your S.O. are into coffee, you may want to consider stopping in at one of the city’s cozy spots for a latté or good ol’ hot cocoa on chilly mornings. Inkwell Coffee and Teahouse is one popular shop, and the Coffee Pot Restaurant is a local favorite as well. 

The Community Would Be “Glad” To Have You

One of the best aspects of visiting smaller towns, especially on a romantic vacation or weekend getaway, is meeting the friendly people there. Locals in spots like Littleton are often welcoming and full of helpful recommendations to make the most out of your stay. Based on one of their most famous cultural festivities (and monuments), Littleton is no exception. 

“One of our claims to fame in Littleton is that our hometown author, the author of the famous book, Pollyanna was born here on Main Street Littleton,” Veronica said. “Eleanor Porter grew up here in town and went on to write five novels. She was a remarkable woman of the 20th century, and we celebrate her and Pollyanna right here on Main Street.”

Holiday parade in Littleton, New Hampshire
The locals in Littleton gather for plenty of festive celebrations year-round.

An adorable bronze sculpture of Pollyanna sits on the lawn of the library in town, with her arms flung wide open and a big, bright smile. She is one of the town’s most renowned features, and serves as an inspiration for the warm and welcoming community in Littleton. Many tourist groups and visitors have taken selfies with the sculpture over the years, even those traveling from overseas. The Littleton website even mentions that people like to touch Pollyanna’s shoe for good luck.

Each year in June, everyone in Littleton gathers to celebrate “Glad Day.” This celebration recognizes the life and impact of Eleanor Porter, and what she — and Pollyanna — mean to her hometown. In 2022, Littleton’s celebration included the twentieth anniversary of the unveiling of the sculpture, and each year the Glad Day tradition includes ladies young and old dressing up as Pollyanna herself. 

If you and your partner are passing through to visit Boston or just want a calming destination for your first trip together, Littleton is the place to be for outdoor adventures, seasonal sights, and plenty of local eateries and events to enjoy. Love is a beautiful thing, so enjoy “falling” right along with the leaves.