5 Fun Day Trips in Boston and New England 2024
If you are visiting Boston and looking to do some day trips while you are visiting or do a staycation here are some fun ideas for the family to jump in the car (or even a ferry boat) to spend the day exploring a new local place in New England.
Kennebunkport Maine
A favorite spot for many is, Kennebunkport is just 90 minutes north of the Boston. Famously known as the summer vacation of the Bush family. You can can see their compound on
Walker’s Point from the water, the lovely town offers plenty of shopping, like the aptly named Daytrip Society boutique. You’ll have your pick of lobster rolls in Maine, but brave the line and opt for one doused in butter and mayo at The Clam Shack on the Kennebunk Bridge. For a more formal meal, head 15 minutes outside of town and dine at renowned chef Ken Oringer’s Earth at Hidden Pond resort. The rustic-meets-luxury lodge is one of the best of Maine.
History buffs will love viewing the historic sea captain mansions that line Summer street, local museums including the First Family exhibit on the Bush family with a tribute to the Presidential Bush comoun, amid the splendid summer cottages that grace Ocean Ave. A wonderful collection of historical artifacts are kept at the Brick Store Museum and the Nott House, while train enthusiasts will love the world famous Seashore Trolley Museum in Kennebunkport.
There are many opportunities for boating adventures, located directly in town. Whale watching tours are popular attractions in Kennebunkport for visitors who hope to catch a glimpse of one of these large and magnificent creatures out at sea. Whale watch trips from Kennebunkport travel about 17 miles to Jeffrey’s Ledge to spot whales. Other tour boats take guests on hour to two hour fishing or lobstering excursions, where you can experience the life of a fisherman first-hand and get a close up view of Walkers Point where President Bush resides and even pull up a Lobster Trap. Kennebunkport also offers scenic sailing cruises, such as on a beautiful Maine Schooner or Windjammer, that travel along the coastline for a relaxing day trip or sunset sail. There are also several rental places in town which allow visitors to rent kayaks, canoes, boats, bikes and even scooters – for a few hours or the whole day!
Dock Square, the center of town in Kennebunkport, is known for its quaint boutiques and local craft shops, selling everything from souvenir shirts to hand crafted jewelry. Dock Square is also home to many highly rated restaurants including Striper’s where the Bush family dines and the Clam Shack which has appeared on the Food Network for its famous lobster roll, fried clams, and mouth watering seafood. Local favorites include Alissons in the heart of Dock Square and Old Vines Wine Bar. Kennebunkport is also home to fancier, special event dining that is definitely worth the extra spending. The White Barn in Kennebunk is New England’s only five star, five diamond restaurant, a truly unique and unrivaled culinary experience with a five course price fixed menu.
Concord and Lexington
The British might have deemed these two towns worthy of a fight in 1775, but modern-day visitors appreciate Concord and Lexington, just twenty miles west of Boston, for their bucolic beauty. Henry David Thoreau spent two years in a cabin on Walden Pond here, and you can take a cue from the writer, too. Pack a picnic and find a spot for lunch on the five-mile Battle Road Trail.
One convenient way to start your tour is to enter the center of Lexington, park your car, and board the Liberty Ride, a bus ride through the high points of the story of the opening battle of the Revolutionary War. The bus tour includes Lexington Battle Green, Munroe Tavern, the National Heritage Museum, Minute Man National Historical Park as far as North Bridge, the Paul Revere capture site, Battle Road, Orchard House (the home of Louisa May Alcott), Colonial Inn, the Old Manse, Concord Museum, The Wayside, and Emerson House. Tours operate April through October.
A drink or meal at Concord’s Colonial Inn, 48 Monument Square in Concord, is a great way to rest and absorb the flavor of Revolutionary times. Listed on the National Register of Historic Places, the original structure was built in 1716. The property has been operated as a hotel since 1889. Situated on Concord’s town common, known as Monument Square, the Inn is surrounded by landmarks of our nation’s literary and revolutionary history.
Portsmouth New Hampshire
Portsmouth is a vibrant, coastal New England city that honors its colorful history, preserving its authenticity while remaining passionately engaged in shaping its future. Its working seaport, unique locally owned shops and restaurants, world-class culture, engaging outdoor activities, vibrant nightlife and interesting local character attracts visitors from around the world, year-round. The whole-life, healthy environment of this walkable regional capital provides the catalyst for residents and visitors to enjoy a unique urban experience within a sustainable and progressive business environment. A smart wise person will ditch the car upon arrival in Portsmouth to enjoy this walkable city!
Shop in unique downtown shops and boutiques in downtown Portsmouth, and find your favorite brand stores just next door. Portsmouth boutiques and specialty shops are 99% locally owned and operated, and have made Portsmouth a virtual cornucopia of styles and tastes. Stroll downtown and discover some true treasures for every member of the family
Portsmouth for dinner on the decks, or at one of the historic restaurants nestled on Ceres Street.
Black Trumpet Bistro: Formerly known as the Blue Strawbery, Chef James Haller opened the first restaurant on Ceres Street in the early 1970’s and laid the founding bricks of culinary destination that our city is today. Portsmouth, known as a lowly and even dangerous town transformed into a sought after dining experience among folks near and as far as Europe. Eventually, the restaurant turned into Lindberg’s, and now the Black Trumpet bistro owned by Chef Evan Mallett.
Oar House: Where it is thought that the tunnel entrance in the back of the dining room connected to Moffat Ladd house across the St. Mr. Moffatt and son Ladd were big into trading with the East Indian companies and islands with lots of goods coming in to Portsmouth.
See more about Vintage Christmas in Portsmouth
Salem Massachusetts
Salem is The people of this Salem relish their rich history and now the town is billed as the Northeast’s Bewitching Seaport. This town is where the famous witch trials were held in the 1600s. Arthur Miller wrote about these trials in his famous play, The Crucible. Today there are plenty of psychics and fortune tellers on hand who practice their craft free of reprisal and the Salem witch museum is the town’s most popular attraction. The town has many historical sites still preserved from the famous witch trials of 1692. Salem is such a fun car trip away.
Boston Harbor Island Hopping
If you are anything like me, you have never taken full advantage of the fact that we have an amazing National Park right off the coast of Boston. The park is comprised of 34 small islands (11 of which are open to the public) just minutes away by boat. The islands vary as far as what you can do on each of them, so use this list as a guide to get you started. The National Park Service recommends picking no more than two islands to visit in one day, so take a look and choose one or two that look interesting to you. Concession stands are available at Georges and Spectacle Islands, but why not bring a picnic lunch for your visit to the islands! It’s a perfect excuse for a picnic! You can catch the ferry from Boston Long wharf or from Hingham (limited weekdays)
Find the best price hotel in the area if you decide to stay overnight
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