Customized Group Tours
Experience Littleton with a tour tailor-made for your group. Leave all the planning to us and kick back to enjoy all the fun Littleton has to offer!
Named a Best Small Downtown in America by Best Choice Reviews and Travel & Leisure’s list of America’s Greatest Main Streets, Littleton delights visitors with its small-town charm and ambiance, walkable downtown with interesting shops and historic buildings and plenty of things to see and do.
Tell us what kind of activities you’re interested in and we’ll put together a customized itinerary tailor-made especially for you and your group with lodging/dining/shopping/activity recommendations to make it a fun, memorable trip.
Here's a sampling of our tour itineraries....
Discover Littleton: Littleton is more than just our renowned Main Street. Discover Littleton’s other neighborhoods featuring unique shops, dining, breweries, pretty parks, a horse cemetery, historic Opera House, America’s oldest ski shop and more. Sign up for our Discover Littleton tour and really experience all Littleton has to offer. Upon arrival in town, we’ll greet you with a private welcome reception and provide you with a tailor-made itinerary and map of outstanding activities. We’ll help with dining/lodging reservations, as well as answer any questions your guests may have during their visit.
Start your day off with a homemade breakfast at one of our Main Street diners, then work off those pancakes with some shopping. You’ll find over 30 unique downtown boutiques and shops. Enjoy a scenic walk along the Ammonoosuc River - where you can walk across both a covered bridge and a suspension bridge - to boost your appetite for a festive lunch at one of our local eateries. After lunch, enjoy a presentation by one of our hometown experts on everything from Littleton history, cooking, wellness, outdoor rec, grilling and of course, Pollyanna, the fictional character whose author grew up in Littleton. Make it a relaxing getaway - park your car and spend a few nights lodging downtown and enjoy different dining experiences each day without ever getting in your car. Littleton is an award-winning, walking-friendly community. Everything you need is within walking distance of downtown
Littleton is a wonderful place to host a bridal/baby/bro/gals’ getaway. Bring your friends and we’ll arrange a venue to host your party with catering and special surprises. Add in some time for shopping, spa services, hiking, biking, yoga, and dining to make it a special friends’ weekend to remember for years to come.
Before it was incorporated in 1784 as Littleton, the town was originally known as Chiswick, the Saxon word for Cheese Farm, and then Apthorp before being named in honor of Colonel Moses Little, who held the post of Surveyor of the King’s Woods. If you enjoy history — we’ve got plenty. The Littleton Historical Society has presentations, displays and a walking tour to make any historian smile. Plan a trip to enjoy a special dining experience along with historic stories and tours.
Glad Town Tour
Littleton is known as the Glad Town in honor of our hometown author, Eleanor Porter, the author of Pollyanna. Pollyanna was known for her exceptional optimism, and that positive spirit is captured in a cheerful bronze sculpture right on Main Street. Learn the history of this popular story followed by a visit to the Glad Shop for some laughs and fun photo opportunities.
Dog Day Out
Bring your doggie friend to Littleton and visit pet friendly shops, restaurants and trails. Stop by a pet boutique for a special treat for your fur baby. You can even book a special photography session for your pet as a keepsake of your visit.
Discover easy (or challenging) local hikes with spectacular views. Find walking and biking trails all over Littleton. Many are easy, near downtown and feature bike repair stations, great food and breweries. Bike rentals are available, too, with maps and guides as needed.