Wander Always & Stay Wilde


4 Day Trips from Boston, Massachusetts

If you have ever traveled to New England, you may have noticed how close in proximity the states, cities, and towns are to one another. Boston is one of those central locations in the northeast portion of the United States and New England. From its city borders, you can drive north, south, and west to countless locations for day trips! While spending an entire week in the city with my family, some days we explored the downtown area, and others we explored outside of the city limits. Continue reading to see where else was visited during the week- the options are endless, which makes every trip to Boston a recipe for new adventures and places to explore!


The White Mountains of New Hampshire are a year-round destination for outdoor enthusiasts and families exploring the area, and the perfect destination to visit while in Boston. The scenery could not be more of a juxtaposition from downtown Boston- trading a landscape of highrises for mountains and forests. Although every season offers a new perspective of the stunning scenery of the mountains in New Hampshire, this area of New England truly shines in the autumn months when the colorful foliage comes to life. The White Mountains are a part of the Appalachian Mountain Range and are considered to be the most rugged mountains in all of New England, covering roughly 1/4 of the state. While in the area, we explored the Flume Gorge at Franconia Notch State Park and drove the Kancamagus Highway, stopping at the scenic overlooks for some leaf peeping along the way.

We clocked our drive at 2 hours and 2 minutes from Boston to the visitor center in Lincoln, New Hampshire. From there, you can drive an additional 8 minutes north to the Flume Gorge. The drive to the other side of the Kancamangus Highway from Lincoln is just over 35.6 miles ending in Conway, New Hampshire.


At roughly eight miles of land that stretches near Interstate 93 of Northern New Hampshire, Franconia Notch State Park is a nature preserve in the White Mountains and a must-see spot in this area! The park is named for the Notch that passes through the Kinsman and Franconia Mountain Ranges in the White Mountains. The park is known to many as the home of the Flume Gorge, a natural gorge that extends 800ft at the base of Mount Liberty and the granite walls of the gorge extend to roughly 90ft high and up to 20ft wide.

We drove straight to the Lincoln Visitor Center nearby from Boston, and this was a great location to refuel, grab something to eat, use the restroom, and have phone service in an otherwise spotty area within the mountains. We ordered some sandwiches at Moon Bakery Cafe, just east of the visitor center, and they were great! While at the visitor center, we made reservations and purchased tickets online for our visit to the Flume Gorge. At this time, reservations are required to keep track of the number of visitors entering the park per hour, and there are a limited number of reservations per hour. I suggest if you are able, to visit as early as possible for a less crowded experience. The trail is quiet and peaceful and easy for hikers of all ages. With your reservation, you can enter the park at any time within the hour selected.

The ticket to Franconia Notch State Park does not only include the visit to Flume Gorge- the hike is filled with a few covered bridges, some waterfalls, and countless stunning views along the 2-mile hike. This is a “can’t miss” location to see if you are in the Boston or White Mountains area, especially with all of the beautiful fall foliage!


The Kancamagus Highway, a National Scenic Byway, runs for 56.39 miles east-west in northern New Hampshire. The section of Route 112 that we drove, starting west in Lincoln to the east in Conway through White Mountain National Forest is only 35.6 miles. The highway climbs nearly 3,000 feet offering spectacular and dramatic views along the way. Simply driving through from Lincoln to Conway takes roughly 47 minutes, but along this road, there are hiking trails, campgrounds, designated scenic areas, and numerous overlooks. Allow some time to stop and enjoy the views. I highly recommend the Sabbaday Falls trail and the Rocky Gorge & Lower Falls areas. I previously visited these sites when visiting in the summer months- click here to read more about the overlooks and trails along Route 112.

List of overlooks & hiking trails along the highway:

Lincoln Woods

Hancock Overlook

Pemi Overlook

C.L. Graham Overlook

Sabbaday Falls

Sugarhill Overlook

Rocky Gorge & Lower Falls



About 2 hours and 4 minutes north of Boston I95 North will take you to the quaint city of Freeport, Maine. Home to the L.L. Bean Flagship Store and Headquarters, this is the perfect place to spend the afternoon and explore if in the area! The actual headquarters warehouses are just down the street, but the L.L. Bean main campus is comprised of different buildings for departments of their brand: an example being a separate building for “Home” and another for “Bike, Boat, and Ski.” The Flagship store on the campus, featuring their classic Bean Boot and apparel, is open 24 hours a day, 365 days a year! There is a cafe right by the “Famous L.L. Bean Boot” where you can grab a snack or coffee while walking the campus and the nearby outlet shops. Although this area is probably beautiful in every season of the year, I highly suggest visiting in the fall. During my visit, the leaves were close to peak foliage and the weather was crisp and perfect for a sweater and light jacket- the perfect ingredients for exploring the surrounding area on foot!

We happened to visit Freeport on the right weekend! Each year on the first weekend of October, 175 of the best New England artists, makers, and local food producers gather together for a 3-day festival on the L.L. Bean campus and area. It was serendipitous that we visited the area during this time! The area was very crowded and parking lots were packed, but it was all worth it to see Freeport come to life. While in the area, I highly recommend visiting the L.L. Bean outlet store located in Freeport Village Station. This trip, I scored some waterproof boots for 60% off- what a steal!


After a morning and early afternoon spent enjoying the Fall Festival and local shopping in Freeport at the L.L. Bean Flagship and Outlet stores, we drove about 35 minutes northwest to Wiscasset for a late lunch/ dinner. After a bit of research on where to order a lobster roll in the area, we found that Red’s Eats in Wiscasset was on every “must eat here” list. Red’s Eats was named Trip Advisors Travelers’ Choice Best of the Best in 2020, and it did not disappoint. This was a repeat visit for me and my father! Thankfully, I knew what to expect during this visit. The line was over an hour long, but it was worth every minute of the wait! Our group each ordered a lobster roll and I opted for the crab cake platter as well. It was just as good as I remembered, especially the locally sourced butter that is served with each lobster roll! I was overjoyed to share this culinary experience with my mom and sister, as they share a love for lobster rolls!

Also, important to note- that my sister and father heard that there was a pop-up that served oysters on the same street where we were waiting in line. While waiting and holding their place in line, they enjoyed half a dozen freshly shucked oysters, which they said were very good. Check out “Brother Shucker“ while you visit Red’s Eats!

To read more about my previous trip to Freeport and Wiscasset, check out this post.


Just a short drive from Boston, located 34 minutes from the downtown area, is the seaside city of Salem, Massachusetts. Known for the witch trials in the late 1600s and the set location for the cult-favorite movie Hocus Pocus, this is such a fun place to visit in October! Due to traffic and crowds, we did not get to explore much of the city center area, but we did enjoy a lovely lunch at Sea Level Oyster Bar, visited an antique shop, and drove around the local streets enjoying the scenery. If you are visiting in October and you are driving in for the day, I suggest an early morning start to explore some of the famous sites (and Hocus Pocus filming locations) throughout the town before the crowds start to pick up in the afternoon.


Our concierge at the hotel we stayed at in Boston gave us some wonderful culinary recommendations while we explored Boston and the surrounding area. When we mentioned our visit to Salem, she immediately suggested Sea Level Oyster Bar. Its location is toward the historic side of Salem, a more quiet section than the tourist area where crowds mainly tend to visit. It was the perfect spot for a scenic lunch! The food was excellent. We ordered the Baked Seafood Pie, the Crab Cake Sandwich, and the Baked Atlantic Scallops (pictured respectively). We were seated on the second-floor covered balcony that overlooked the wharf on a picture-perfect afternoon. I would definitely visit this restaurant again and will be recommending it to anyone I know visiting Salem.

Sea Level Oyster Bar is located at 94 Wharf St, Salem, MA 01970.

After lunch, we decided to drive around the local streets of Salem before heading back to Boston. We were close in proximity to the House of the Seven Gables (made famous by Nathaniel Hawthorne’s 1851 novel). Tickets are required to tour the house and the garden area, but we opted for just a quick walk around the perimeter for a peek at the grounds. We will be back in Salem at a less busy time of the year to visit the sites!



As the oldest institution of higher learning in the United States, Harvard University was first established in 1636 and is among one of the most prestigious universities in the world. With its location being in such proximity to the downtown Boston area, we knew it would be the perfect spot to visit. We walked about 15 minutes from our hotel room in Boston to South Station, where we purchased tickets for the Red Line subway to our destination of Harvard Square, which, with 6 stops, took about 17 minutes to our destination. The Harvard Square stop on the Red Line takes you right to the gates of Harvard University – so convenient! Since it was a slightly dreary day, we walked around the campus for an hour or so exploring the architecture and grounds of the University, but it was worth the stop! As the rain slightly picked up, we stopped in a few of the shops in the surrounding area as well as the Harvard bookstore before eating lunch at Tatte Bakery and Cafe.


Tatte Bakery and Cafe was hands down our favorite spot for a quick bite during our entire week spent in Boston and the surrounding area. The Cambridge location was our first experience of this cafe, and after that, we proceeded to eat at 3 other locations we passed (mind you, there are 17 locations in the Boston and surrounding area alone!). This is a definite “must-visit” while in the area. There are excellent baked goods offered as well as breakfast and lunch entrees to enjoy either dining in or taking out. We ordered an array of baked goods – all of which were delicious – as well as the Proscuitto and Fig Pannini, the Short Rib Grilled Cheese, and the B.L.A.T. (BLT with avocado). There are so many things on the menu that I would love to try, so I guess that means I will need to plan a return visit to Boston soon!

Have you ever traveled to Boston or anywhere in the surrounding area? What are your favorite places to visit, stay, and eat?

Have you been to any of the places listed in this post? Comment below!

If you are traveling to the New England and Boston area soon, I hope this post can help with planning your adventure. Happy and safe travels!

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