A Driving Itinerary for an Epic New England Road Trip (Including Hotel Recommendations)

Let’s be honest. No one is boarding a plane for paradise anytime soon. So when can we travel safely again? It is hard to predict, but I am hopeful that some travel will return this summer and fall. As to where to vacation in 2021, I think that a New England Road Trip is a pretty terrific option.

“… the maples wear a gayer scarf, the field a scarlet gown” (Emily Dickinson)

New England is certainly made for road-tripping- the region packs a lot into a remarkably compact area. And there are almost too many reasons to love this little corner of the world. The history of New England is the history of America. The region is also breathtakingly beautiful with blazing fall foliage, pine scented mountains and a seemingly endless Atlantic coastline which brings picture perfect views and the promise of killer seafood.

I just finished writing the 4th edition of my book Day Trips New England (releasing in June and available for pre-order!) which offers 50 pre-planned itineraries throughout the region and is packed with hundreds of picks for things to see and do.

Consider this Day Trips New England’s bonus chapter.

For first-time visitors, I have mapped out a 2 -week itinerary which begins and ends in Boston (as all things New England generally do) and includes visiting Rhode Island’s coast and its glamorous Newport Mansions, the cultural attractions of Massachusetts’ Berkshire Hills, the mountains of Vermont and New Hampshire, along with Portland and coastal Maine.

To help you plan your perfect trip, I offer some of my favorite places to stay along the way. Most are independent hotels and family-run inns. They are the kinds of places that offer a real sense of New England’s heritage, and as many are in the $200-$300 a night range, they are affordable.

Understanding Yankeedom can take a lifetime, but on this journey you will get a good appreciation of what makes New England singularly unique. It’s an ambitious itinerary but the sites are magnificent, the scenery is fantastic and the open road beckons!

Note: Of course, always follow national and state travel recommendations regarding Covid-19 when you travel.

Boston, Massachusetts- 4 nights

Boston’s charming Beacon Hill

All roads in New England lead to Boston. Established in 1630, (nearly 400 years old!) Boston is considered the birthplace of the American Revolution and the city that made the nation. A powerhouse in the fields of health care, education powerhouse and tech, Boston is forward thinking and one of the country’s most progressive cities.

The city is extremely well-positioned within easy driving distance of the rest of the region.

Top experiences include walking in the footsteps of the Founding Fathers along the Freedom Trail, being part of Red Sox Nation for a game at Fenway Park, exploring the lantern-lit cobblestone streets of Beacon Hill, and enjoying wicked good seafood at a waterside table. With 4 days you have enough time to see most of the sites with out feeling rushed. Another option? Spending a day visiting the towns of Lexington and Concord and the Revolutionary War sites at Minuteman National Park.

Boston Park Plaza Hotel. This historic hotel has been welcoming travelers since 1927. Superbly Located in the Back Bay, this is still one of the biggest hotels in the city- and because it has more than 1000 rooms to fill, it almost always has some bargain rates. The lobby eye-catching white lobby with original chandeliers is modern and luxe and rooms have recently been totally refreshed in boutique- style black,white and grey.

The Revolution Hotel. One of the city’ s newest properties, this South End hotel challenges the status quo of Boston hotels with hip, budget -friendly rooms that feature king, queen, or two double beds. There are even quad rooms with two sets of bunk beds. Most rooms have a compact, private bathroom, but there is an option to save even more money by booking a room only and using one of the bathrooms down the hall. It’s a little bohemian, but a good option for Millennials for whom AirBnB has lost its appeal or for large families that don’t want to do the Embassy Suites- thing.

The Kendall Hotel. A not-so secret affordable Cambridge hotel, this gem is housed in a converted firehouse and features artwork commissioned by local artists. The 74 rooms feature a spare modernist style with homey touches like handmade quilts on the beds. Rates include a continental breakfast and a nightly wine tasting where you may just mingle with creative types from the nearby Kendall Square tech companies.

Newport, Rhode Island- 2 nights

Rhode Island is the country’s smallest state, but its nickname is “The Ocean State” partly because it has nearly 400 miles of Atlantic Ocean coastline. Once upon a time, Newport was the summer resort of choice for 19th century robber- barons. Today, visitors come to gawk at the over-the top splendor of Gilded Age mansions, experience yachting culture on Narragansett Bay, and enjoy stunning beaches and top-notch dining.

Of late, Newport is in the midst of a mini-hotel building boom which has had the effect of lowering room rates throughout the city.

The Hotel Viking. Built in 1926, this beauty of Golden Age glamour offers both luxury and location- and won’t break the bank. Located in the center of the historic district, the 200 +classical inspired rooms lean toward the cozy side but offer all the modern amenities including pillow top mattress, high-count sheets and LCD TV’s. Bonus- there’s an indoor pool.

Wayfinder. Opened in 2020 by a group of local chefs and artist -types and located in the quiet northern part of Newport ( across from Miantonomi Park) this a food- forward hotel for the thoughtful, budget traveler. The 197 rooms are uniformly large featuring all blond wood, fluffy white bedding and succulents. The onsite Nomi Park restaurant features casual, all day dining like a half chicken with harissa and tahini roasted eggplant.

The Inn at Mount Hope Farm. Just 15 miles to the north, the historic coastal town of Bristol is an under-the-radar and super thrifty choice to avoid the crush that is Newport. The 1745 Governor Bradford House is a B & B ( with 12 nest-like rooms) that is part of Mount Hope Farm. Enjoy the perennial gardens, extensive property walking trails and visiting the goats and chickens in the barns. Guests will find wide plank floors, massive fireplaces, antique four -poster beds and a phenomenal cooked-to-order breakfast- all for the paltry sum of less than $200 per night. (A personal favorite!).

The Inn at Mount Hope Farm

The Berkshires- 2 nights

Tanglewood (the summer home of the Boston Symphony Orchestra), Jacob’s Pillow Dance Festival, the Williamstown Theatre Festival, the Norman Rockwell Museum and Edith Warton’s home the Mount, Butternut and Catamount for skiing and hiking Mount Greylock are just a few highlights of the cultural mecca known as “The Berkshires”. The Berkshire hills are located in the western part of Massachusetts, practically equidistant between New York City and Boston (and it may be the only place in New England where a Yankee hat is tolerated).

The Red Lion Inn. One of New England’s oldest inns (dating from 1773), the 125 rooms offer comfortable, historic charm. Even if you are not staying – drop by to spend some time rocking on the hotel’s famously beautiful front porch with a drink and take in the Rockwell-like scene of small town New England. (In fact it really is, as Norman Rockwell lived in Stockbridge and based many of his painting on life here).

Old Inn on the Green

Old Inn on the Green. Located in the town of New Marlborough, this white painted, wide -porched 1760’s former stagecoach relay station is set against a forest backdrop and is an absolute treasure. With just a handful (11) of elegantly rustic rooms, guests enjoy warm hospitality from husband and wife team Peter Platt and Meredith Kennard. Platt is also a renowned chef and local ingredients feature at the inn’s dining room which is entirely lit by candles-it’s the sort of meal that you remember for a lifetime. Unexpected- the property also boasts a small swimming pool.

Tourists. Once a seedy road side motel along the Mohawk Trail, this new-ish (it opened in 2018) 47-room property has an unmistakable hipster sensibility with modern, mindfully minimal rooms (white linens, light wood, large windows that look out to the trees) and the requisite bonfire pit. The hotel offers tons of outdoor activities (hiking, yoga, crafts) on its 80-acre campus and there is an excellent onsite restaurant too. Another bonus? Pets are welcome here.

Burlington , Vermont- 2 nights.

The Green Mountains state is known for its craft breweries, artisanal cheese and skiing. There are rolling hills, idyllic farmland, charming village greens and gorgeous fall foliage. Yes, storybook Vermont really does exist.

Willard Street Inn. A local fixture, well-known as an affordable option for a characterful stay in Brulkingon.The 1881 mansion was once a private home and is located in a leafy, residential neighborhood, but is still walkable to downtown. Each of the inn’s 14 restful rooms ooze with antique charm. The stunning solarium has 317 glass window panes and is a wonderful spot to have the (included) cooked-to-order breakfast. Parking is free too.

Field Guide. Just 30 miles east of Burlington and situated in the Green Mountains, Stowe is the ski capital of the East. Field Guide is a modern ski lodge inn (with just 30 rooms) that strikes the perfect balance between rustic and modern. Each of the rooms is decked out with contemporary artworks, eclectic touches like live- edge wood headboards, and a smattering of vintage finds. There’s a swimming pool, hot tub and outdoor fire pit. Rates include breakfast.

Shelburne Inn. Can you tell that I have a penchant for historic properties? Located just 20 minutes south of Burlington, this spectacular historic 19th century mansion is set along the shores of Lake Champlain. This is a 1400-acre working farm (and a very fancy one at that) with grounds that were designed by Frederick Law Olmsted. There are also several barns, a cheesemaking operation, miles of natures trails and an excellent farm-to-table restaurant. The inn is opened during the summer only and offers 24 adorable rooms and 4 cottages; rooms do not have TV’s and rates are from $175 per night.

White Mountains, New Hampshire- 2 nights

“Live Free or Die” is the Granite State motto; which perfectly sums ups New Hampshire residents; self-reliant, stoic and thrifty. The White Mountains are the ultimate destination for outdoor enthusiasts with miles of hiking trails including brooding Mount Washington, which at 6300 feet, is the East Coast’s highest summit. After a day outdoors, relax sitting lakeside or fireside at any number of the region’s inns and restaurants.

The Mount Washington Resort. This historic palatial hotel (it has nearly 400 rooms) has that vintage- resort grandereau vibe in spades. Built in 1902, the red-roofed gabled Renaissance Revival was a favorite retreat for Gilded Age families. Once you check in, here you may not want to leave. And as it turns out, you many not have to. In summer there is golf, a spa, indoor and outdoor pools, stables, zip-line canopy tours and tennis courts. In winter, there is skiing at nearby Bretton Woods, tubing and sleigh rides. Now part of the Omni hotel chain, the hotel has undergone a recent expansion that includes 69 modern rooms with balconies against the backdrop of the White Mountains. Pricey? Yes. But the Mount Washington is a bucket-list hotel that is totally worth the splurge. (It’s beloved by our family; summer or winter).

The Sugar Hill Inn . One of the most seriously romantic New England Inns that you will ever come upon. Built as a small farmhouse in 1789 and expanded many times over the centuries, this is a rambling, luxurious and relaxing place to stay. It is also one of the best fine dining rooms in the Granite State, so take advantage of the inn’s dinner/lodging packages when you book. The 14 guest rooms and cottages are furnished with an era-spanning mix of antiques and fine furnishings; some rooms have fireplaces, whirlpool tubs and/or private porches looking out to Mount Washington. Rates include a gourmet full breakfast as well as evening small bites and drinks. Note: the inn does not allow children under the age of 14.

Scenes from the Hancock Inn

Hancock Inn. As an alternative to the barrage of nature and adventure activities in the White Mountains, I offer the low-key option of heading south along curvy country roads to New Hampshire’s Monadnock region. Here you will find vast woodlands, mountain views and small town charm to spare (the town of Peterborough was the inspiration for Wilder’s play “Our Town). The grey clapboard Hancock Inn is one of my all-time New England favorites, offering guests exceptional hospitality along with creaky floorboards, exposed ceiling beams and 14 handsome rooms. Rates include breakfast and the onsite Fox Tavern tempts with New England classic dishes like pan seared duck breast and parsnip puree or roast pork loin with sweep potato hash.

Portland, Maine- 2 nights.

Maine is big-it’s nearly as big as Massachusetts, New Hampshire, Vermont, Rhode Island and Connecticut combined. The drive to Maine is reliably uncrowde ; a study in contrasts among rock, sea and forest. And at the end of the day there is lobster- always lobster.

Maine lobster chowder anyone?

Inn on Carleton. Those who would rather spend their money on a great Portland meal than on their hotel room love this West End townhouse inn with its 6 design-driven, historic-yet contemporary rooms which feature plush bedding, fireplaces and original molding details.The included two-course breakfast (featuring menu items like frittatas and granola parfaits) is a highlight of every stay. All in all, it has the feel of spending the night at family friend’s home.

Portland Regency. A good choice for the budget conscious, this 95-room hotel offers rates considerably lower than other Old Port District properties. Once an armory, rooms are done up in a neutral, modern businesss hotel style, but it is the onsite spa and fitness room set it a part from other Portland hotels.

The Harraseeket Inn. Head north 16 miles from Portland to Freeport and you’ll find this family-run 94-room country inn which is perfectly situated for exploring mid-coast Maine. Rooms come in many shapes and sizes and are consistently decorated in a cheery traditional New England style. Rates include a la carte breakfast at the excellent onsite Broad Arrow Tavern and there is an indoor pool as well. Making the pilgrimage to L.L. Bean’s headquarters? The Harraseeket Inn always has on offer excellent lodging/dining/shopping packages.

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