I've visited Boston and New England a few times being I have relatives in Boston. While Boston is a magnificent city to explore, there are smaller, quaint little New England towns (some with cobblestone streets!) that let you feel like you stepped back in time.
So I designed a 7 day road trip itinerary that will highlight some of these smaller towns that offer history, shopping, art and culture, fantastic scenery and cozy charm. With the exception of Bar Harbor, you would spend a night in each of these towns - but you adjust your road trip itinerary to suit your needs!
I've designed the road trip to show you the best of all of the different landscapes New England has to offer.
If you're flying into Boston I recommend you fly into Boston Logan International Airport because they have the cheapest flights into Boston. You can use the link above to search flights and it will also give you travel options to get to and from the airport. Not only that, this city also incredibly convenient to most places in New England, and is centrally-located in the region, and therefore, is just the easiest starting point.
If you're driving in, I still recommend starting in Boston, especially if you've never been there before. But if you're driving in you can adjust your starting point to wherever you wish.
Boston Accommodations
Boston is expensive and I wanted at least a 4 star hotel at more inexpensive prices, in downtown and near the Freedom Trail and Boston Common. I found the perfect boutique hotel (all recently renovated) in the Godfrey Hotel at 505 Washington Street.
The Godffrey is modern but with a relaxed atmosphere. The rooms were large enough and comfortable, the bathrooms spacious, everything very clean. Best of all, the room was super quiet.
The service was superb, The hotel also has a really nice gym, spa services and valet parking.
It's George Howell Coffee shop was great and so handy. The café at the Godfrey Boston features an espresso bar, specialty coffee-based creations, and more. In addition to estate coffees, guests enjoy a wide selection of pastries, sandwiches, and local products.
Serving fanciful cocktails, a carefully selected variety of wines and local beers, the Lobby Bar is the perfect way to begin or end your night on the town.
RUKA restaurant (right next door) is an exploration of Peruvian-Japanese culture that embraces the exquisite presentations and bold flavors of Nikkei cuisine.
By taking advantage of their special Stay More & Save More offer and booking 3 nights, Monday through Thursday I saved 30%. (Book directly through the hotel)
The other option I like is the Revere Hotel Boston Common. It's a great location because so much is within walkable distance. This is another 4 star hotel at affordable prices. Be sure to check out their special offers!
Italian-Mediterranean feasts await in the hotel’s Rustic Kitchen Bistro & Bar. New England cuisine is available at Rebel's Guild. Elevate your experience with cocktails at the rooftop lounge, boasting panoramic views of the Back Bay and South End.
The hotel has a self-park secure parking garage ($43 per night) and valet parking. There's a fitness center and laundry services.
OTHER 4 STAR REASONABLY PRICED HOTELS:
Transportation
I'm not a fan of driving in Boston. It's a nightmare overall. Luckily, Boston offers a robust public transportation system known as the MBTA ("the T"), along with various other options for getting around the city efficiently.
Boston's most popular public transportation options include the subway (usually called the "T"), bus, commuter rail, water taxis, and ferries, all under the management/regulatory umbrella of the Massachusetts Bay Transportation Authority (MBTA).
If you're here just for a visit, you're most likely to use the T and water taxis, plus several other ways of getting around: rental cars, land taxis, Boston's bike-share program ("Hubway"), city tour trolleys, and of course the easiest and cheapest of all: walking.
Boston's compact size means you can walk to most tourist, cultural, and entertainment destinations in less time than retrieving your car from a hotel parking lot would require - not to speak of the hassle of navigating through Boston traffic and then finding and paying dearly for parking near your destination.
-
How to Get Around Boston - All the ways to get around the city: subway, water taxi, bike shares, hop on hop off trolleys, & more
-
More Ways to Get Around Boston - Hop on hop off trolleys & more!
Boston Attractions
The best way to begin exploring Boston is to walk the Freedom Trail. Some choose to walk the entire 2.5 mile trail (about 4 hours), end to end. Others select a handful of sites of particular interest and focus on those places.
If you're only going to spend one day in Boston, then I suggest picking out the attractions on the Trail that appeal to you. My favorites were Boston Common, Boston Massacre site, Paul Revere House, the Old North Church and especially the USS Constitution and its museum. If you can squeeze it in, also stop at The Old Corner Bookstore.
The National Parks of Boston have developed a FREE Freedom Trail® Audio Tour for visitors. This tour is available online on the Freedom Trail® Audio Tour webpage, or by downloading the NPS App. Once downloaded, search "Boston National Historical Park" and select "self-guided tours."
The Freedom Trail Audio Tour is also available in Spanish and French online and on the NPS App. Visit Freedom Trail Audio Tour - Español or Freedom Trail Audio Tour - Français to listen to the tours.
GetYourGuide also offers a self-guided tour of the Freedom Trail via an app you install on your mobile device. The app includes audio narration, a live GPS map, and the route from stop to stop. Click here to learn more about this option.
Another option if you want to walk it on your own: print out the Freedom Walk Trail brochure, which provides information on each of the 16 sites. You can also download a copy of the map using this link.
If you're not a big history buff, by the end of the Freedom Trail tour you may be on history overload. My recommendation would be to stop and take a break from the history at the halfway point, which is near Faneuil Hall and Quincy Marketplace.
There are hundreds of shops both inside and outside the three market buildings (Quincy Market, South Market and North Market) and 18 restaurants and 35 colonnade eateries of all cuisines.
If you're going to spend Day 2 in Boston:
-
Stroll along the waterfront areas, especially the Charles Esplanade
-
Walk through the public gardens
-
Ride the Boston Common Carousel
-
People watch at the Frog Pond - a splash pad for kids in the summer
-
Visit the New England Aquarium
-
Visit the Boston Tea Party Ships & Museum
Boston Dining
To get an idea of all the cuisine Boston has to offer, I recommend taking a food tour. Not only do they offer incredible value and insider info on all the best places to eat, you’ll get to sample some of the best food around the city in a short amount of time. Here are 3 I recommend:
1. North End Pizza & History Food Tour
2. North End & Public Market Tour
3. Brewery Tour With Lunch or Dinner
DAY 2 - WOODSTOCK VERMONT (If you choose not to stay in Boston for 2 days)
Woodstock, Vermont
Woodstock has its own charm and plenty to see and do. Woodstock has a wonderful town center, where you’ll find independent shops, cafés, and restaurants, covered bridges, farms, and it’s also surrounded by beautiful rural scenery once you drive outside of town.
Woodstock Accommodations
506 On The River Inn. Very beautiful boutique hotel that’s right on the river and feels cozy.
Just minutes from historic Woodstock Village, On The River Inn offers a warm, relaxed stay for couples, families, and travelers looking to slow down and reconnect. Surrounded by nature and Vermont charm, the inn features comfortable rooms, a farm-fresh bistro, indoor pool, hot tub and sauna, and year-round access to the best of the Green Mountains.
On The River Inn
The Vesper is a cute little B&B with modern rooms, great prices, and walkable to the village.
They serve a continental style breakfast from 8am-9am in the breakfast room: coffee, tea, fruit, spiced steel cut oatmeal, hard boiled eggs, yogurt and granola and baked goods. You can feel free to eat in the breakfast room or take it back to your room.
This is basically a no frills B&B (although 3 of the rooms have Jacquizz's) but the price is really right and inn was clean and comfortable.
Woodstock Attractions
Visit the Middle Covered Bridge which is right in town.
Woodstock's Middle Bridge is the first public covered bridge built by the State of Vermont since 1889. Builder Milton Graton constructed his masterpiece near the crossing, then had it pulled across the river by Ben and Jo, a team of oxen, in July 1969.
Billings Farm & Museum is just a scenic stroll from the village center of Woodstock, Vermont, and is regarded as one of the finest outdoor history museums in the country.
Woodstock's Middle Bridge
Billings Farm 1890 Farm Manager's House
Billings Farm & Museum
Combining a fully-operating Jersey dairy farm with educational exhibits and interactive programs and events, Billings Farm & Museum is committed to providing education and enjoyment to visitors of all ages.
You can purchase tickets online here
Be sure to check out the 1890 Farm Manager's House. It's pretty cool!
Taste local maple syrups and cheeses at Sugarbush Farms - all made right on the farm.
Open every day with free self-tours of the maple sugar house with an educational video about the maple syrup boiling process as well as the other farm work they do throughout the year.
Picnic area, kids play area, and farm animals during the warmer months.
Located 5 miles from historic Woodstock on a scenic town-maintained gravel road. 591 Sugarbush Farm Road.
Visit New England Falconry. (Meets animal welfare guidelines)
Even if you're not a birds of prey enthusiast, you'll find you'll fall in love with these birds fairly quickly. Kids especially love this attraction and being able to be up close to the birds.
The falconry center is located at 4148 Hartland Hill Road, Woodstock. Master falconer Chris Davis has been educating about falconry and raptors since 1985.
The educational content follows the already permitted New England Falconry operation in Hadley, MA. The content of all sessions includes detail about raptor adaptations, conservation, permitting and history of falconry, as well as free flying of Harris hawks and other species to guests.
DAY 3 - WHITE MOUNTAINS OF NEW HAMPSHIRE
Whether you're a photography buff or just love nature and breathtaking scenery, you can't miss the White Mountains of New Hampshire. They're New England's highest peak.
There's adventure around every corner in the White Mountains, for every age and ability! Where else can you zipline through the trees, drive to the top of a 6,288 foot mountain, cruise New Hampshire's largest lake and fit in a winery or brewery tour, all in one day?
For you railroad buffs: Ride the rails along the Pemigewasset River aboard the Granite State Scenic Railway, or traverse Crawford Notch with a ride on the Conway Scenic Railroad's Mountaineer train. Travel through Wolf Man's woods at Clark's Bears, or try pedaling your own rail car a little bit south of our region with Scenic Railriders or Granite State Rail Bikes. With the luxurious meals found on Lincoln's Cafe Lafayette Dinner Train, and spectacular summit views thanks to the marvelous Mount Washington Cog Railway, there are so many options for your signature White Mountains railway experience.
The kids won't get bored either with all of the activities geared toward them.
White Mountain Accommodations
I recommend you stay in Littleton for the sake of convenience and its location to attractions on your road trip.
The most booked accommodation in Littleton is the Hampton Inn. I've been a fan of Hampton Inns since I first began traveling. They're clean, comfortable, have an indoor pool and hot tub, plenty of parking, a free continental breakfast with plenty of options, a game room for the kids, an office center for travelers on business and the rates are reasonable, starting at $198 per night.
DAY 4 & 5 - BAR HARBOR & ACADIA NATIONAL PARK, MAINE
You really need to devote 2 days to this area.
Bar Harbor is one of the most charming coastal towns in New England. There’s something magical about Bar Harbor. A celebrated vacation destination on Mount Desert Island that is the gateway to Acadia National Park, it possesses a rich history and culture unlike any other.
Bar Harbor
PARKING
-
The downtown of Bar Harbor is comprised of a network of four main streets and several narrow side roads.
-
If you choose to bring your vehicle into town, note that from May 15th to October 30th downtown Bar Harbor utilizes a paid parking program which is enforced between the hours of 8:00 am to 9:00 pm, Monday through Saturday, and 12:00 pm to 9:00 pm on Sunday.
-
The parking rates range from $2.00 per hour to $4.00 per hour (depending on location) with certain high-demand areas having 4-hour limits and other areas with no limits.
-
Accessible Parking: Vehicles that exhibit a permanent placard, a temporary placard, or a disability registration plate may park anywhere in a paid or permit area without a charge or permit. For areas with a time limit, these vehicles may remain parked for up to twice the time limit.
-
More details about the program, including how you can acquire parking tokens, can be found on the Town of Bar Harbor’s parking information web page.
Mount Desert Island’s picturesque coastal communities and colorful people are as varied as the island’s scenery. Because of this variety, there is something for everyone to connect to. Bar Harbor is the largest community and offers a great variety of amenities and tourism experiences to visitors.
Acadia National Park can be accessed right from downtown Bar Harbor. The park is one of the most visited national parks in the U.S. It features 45 miles of motor vehicle‐free carriage roads and 16 stone‐faced bridges, each unique in design.
Ride the Cannon Mountain Aerial Tramway to the mountain’s summit for awesome views.
While the Bar Harbor region is best known for its outdoor activities, its small museums, cultural landmarks, and historically significant structures highlight a varied past and present. When it comes to accommodations, visitors will find lodging to suit every travel style and budget, from neatly kept motor lodges to historic inns to luxurious hotels.
My suggestions:
Bar Harbor Inn & Spa: Located in town, right on the waterfront so everything is easily walkable. The Bar Harbor Inn’s beautifully landscaped eight acres offer a private retreat with easy walking access to unique shops, art galleries and waterfront activities. The casual elegance of the Bar Harbor Inn provides a perfect backdrop to explore the rocky Maine coast and Acadia National Park.
Bar Harbor Inn
You have the option of 3 different sections of the hotel in which to book a room.
Main Inn features 50 newly renovated luxury guest rooms and suites. The Main Inn offers four types of rooms: Classic, Bay View, Garden View, and Luxury Suites.
The Oceanfront Lodge offers the ideal location to take in panoramic views of Frenchman Bay from the comfort and serenity of your own private balcony. It too has a variety of rooms to choose from.
The newly renovated Newport rooms at the Bar Harbor Inn are the perfect choice for those looking for an excellent downtown Bar Harbor location and superb hospitality. These lawn and grounds view rooms offer distinctive design and luxury with exceptional amenities and service.
The Bar Harbor Inn offers three unique dining experiences in one spectacular location, a spa, and a swimming pool with fantastic views of the surrounding scenery.
Bar Harbor Villager Motel: An awesome motel in the center of Bar Harbor’s village, with spacious and updated rooms, and walkable to everywhere in town.
This is a good spot if you just need a place to lay your head after a long day of hiking.
Nothing fancy but the motel is clean, comfortable and very reasonably priced. The rooms are cozy.
There's a free continental breakfast and an outdoor swimming pool.
DINING
Bar Harbor is proudly known for its fresh seafood - caught, delivered, cooked, and served straight from the boat - you’ll have more than just lobster making your mouth water. From shrimp, scallops, and crab; to haddock, flounder, clams, and oysters - Mount Desert Island’s sea-to-table options are endless.
To experience tastes from around the world, you can enjoy Mexican, Asian, Italian, Cuban, and of course, American dishes. And don’t forget to indulge in their locally brewed beer and handcrafted ice cream.
Where To Eat In Bar Harbor:
Geddy’s
The Travelin’ Lobster for the best lobster roll in town
Side Street Café
The Stadium for popovers
Mount Desert Ice Cream or Ben & Bill’s Chocolate Emporium for dessert
DAY 6 - DRIVE TO PORTLAND, MAINE
(With optional stops along the way)
In Portland, Maine you’ll find a metro hub with cobblestone streets, nationally-lauded eats, and a scenic working waterfront in the heart of the Old Port. Go from the middle of the action to the middle of just about anywhere with neighborhoods + nearby towns boasting beaches, arts + culture, shops/boutiques, lighthouses, outdoor adventures, and world-class accommodations.
TRANSPORTATION
Portland is easily accessible from I-295 and offers various modes of transportation, including bus, taxi, train, and ferry services. It is also a 10-minute ride from the Portland Jetport (PWM). The city is perfect for walking while enjoying the historic buildings, water views, and working waterfront.
Getting Around Downtown Portland
PORTLAND ACCOMMODATIONS
The Press Hotel. It’s right on the water and in the center of Old Port, making this an awesome hotel to splurge on for a fancier stay in Portland.
This is a pretty cool and different boutique hotel. Inspired by 1920s writers offices, each of the exquisite 110 guest rooms and suites features a vintage-styled journalist desk, wood floors, herringbone area rugs, and local artwork.
When you enter the spacious lobby, you’ll immediately notice the typewriters mounted on the wall and the letters emblazoned on lobby couch pillows. The lobby bar is named the Inkwell, and serves its bar bites on newsprint-lined plates.
As you head to your room, you’ll notice headlines printed throughout the hallway with breaking news.
ACCOMMODATIONS
Where To Stay In Portland: Places for Every Style and Budget
DINING
Alternative for Day 6: Spend the night in a small coastal town.
DAY 7: RETURN TO BOSTON
Portland Regency Hotel & Spa: Also in the Old Port district, this lovely hotel has cozy rooms, a great location, and a nice spa. Located in the heart of Portland, Maine’s historic Old Port district, the Portland Regency Hotel & Spa embodies history, and coastal charm. Housed in a beautifully restored 1895 building—once the Maine National Guard Armory—the 95-room hotel preserves its rich architectural history while offering modern amenities.
This isn't really a narrated tour but the crew can and will answer any of your questions about the sights you're seeing.
The tour lasts 2 hours.
Watch for seals!
Visit Portland's lighthouses. Portland has 3 lighthouses but Portland Head Lighthouse is the must see. It's one of the best lighthouses in New England. It's not only the oldest lighthouse in Maine, it's the most photographed lighthouse in America.
Portland Head Lighthouse
Park staff lead free walking tours at 11 AM daily, weather permitting. The 35-minute talk along the one-mile Cliff Walk Trail includes eight stops featuring discussions on fort structures, native plants, shipwrecks, and lighthouses. Interested visitors should gather at the Greeter's Shed in Central Parking. Tours are limited to 25 people and are available on a first-come, first-served basis. They are not recommended for those with mobility issues.
Shop and dine in Old Port. Don't miss Wharf Street in Old Port, which has an eclectic mix of bars and restaurants along its pedestrian-only cobblestone street. Try Street & Co.'s upscale seafood, The Independent Ice Co.'s fine whiskeys and the Bar of Chocolate's specialty martinis and sweets.
This downtown neighborhood is considered the city's center and bustles with things to do left and right, all the while gracefully maintaining its historical facade. The area is lined with cobblestone streets and 19th-century warehouses, and with the wharf just steps away on Commercial Street, the city's heyday as a world-renowned port town is easily felt. Tourists can benefit from ferries and cruise experiences, as well as the delectable catches aboard the lobster boats that dock there daily.
Go on a brewery tour of Portland's nearly 20 breweries.
Portland is considered by experts to be one of America's best beer cities thanks to its large crop of local brewers as well as its role in the microbrew movement.
For nondrinkers or those looking to take a booze break, check out places like Root Wild Kombucha and Urban Farm Fermentory. They offer a range of nonalcoholic and alcoholic drinks with atmospheres comparable to the breweries nearby.
23 BEST THINGS TO DO IN PORTLAND
DAY 7 - RETURN TO BOSTON
That wraps up our New England road trip. Happy travels!