The ultimate New England travel guide: Where to go, what to eat and how to get there

Last year, I travelled across the Deep South and this year, it was an odyssey across New England. Autumn - or ‘fall’ as Americans call it - is famous in New England: before the trees shed their leaves for winter, thousands of miles of lush foliage sets the tone for a picturesque landscape with leaves turning vibrant colours and officially marking the end of summer.

I visited in the lull period right after the summer chaos had ended and the autumnal rush had yet to begin. It meant that not only were prices more reasonable across the board, but queues were few and far between, and you could experience this beautiful part of North America in its natural glory, and without being overtaken by other tourists.

We spent two weeks travelling around New England on a road trip to remember, flying direct from Dublin to Boston (with Aer Lingus), then driving to Cape Cod, Newport, Rhode Island, New Haven, Connecticut, Portsmouth, New Hampshire, Portland, Maine, then Kennebunkport and two final nights in Boston. On day one, we picked up our rental car from the nearest Hertz dealership in Boston and set out on our merry way.

Boston, Massachusetts

What to do

By now, Boston is well established as home to millions of Irish diaspora and one of the most popular destinations for visitors leaving our small island.

But what makes Boston so special is its unique place juxtaposed between the past, present and future. As one of the oldest cities in America, there is a plethora of activities for history buffs, like the Freedom Trail tour, a two-hour walking tour which visits some of the city’s most beloved landmarks, kicking things off in Boston Common and exploring sites like the Old State House and Benjamin Franklin statue on foot (adult tickets are $14).

For a more modern take on the city’s offerings - and the chance to walk off the Dunkin’ Donuts - we strolled to Fenway Park, through the enchanting Newbury Street (and a brief lunch in Shake Shack), comprising of eight blocks of boutiques, salons and restaurants galore.

Fenway, home to the Boston Red Sox, is open to visitors for a one-hour tour, granting access to ‘America’s Most Beloved Ballpark’ during the bright light of day ($20). A visit to Boston Public Garden is my recommended starting point for day one: sit on a bench, watch the duck tours paddle in the pond and people watch before committing to your itinerary.

Where to eat

Regina Pizzeria: Found in the historic Italian North End, Regina’s is the official pizza of the Boston Red Sox and the most iconic pizza in the state. Huge pies with lots of toppings.

Mike & Patty’s: If you’re a fan of breakfast sandwiches (and particularly egg-based ones) there is no better way to start your day than at corner café Mike & Patty’s. Try the Breakfast Grilled Crack which includes fried eggs, bacon and three types of cheese. Saying goodbye to your arteries has never been so worth it.

Time Out Market: Start off night one of your trip with a curated food hall with some of Boston’s best offerings. Indulge in Japanese fried chicken (karaage) from Ms. Clucks Deluxe or a gourmet lobster roll from Saltie Girl, while sipping on a Bourbon Sour from the bar.

Neptune Oyster: A beautiful raw bar is under your nose with upwards of 12 oyster choices, clams, sea urchins, crab claws and much more. Don’t miss their famed lobster roll cooked in hot butter. They don’t take reservations, so prepare to stand in line (but it’s definitely worth it).

Rare Steakhouse at the Encore Boston Harbor: This is the classic American steakhouse experience: giant shrimp cocktail, any cut of beef you can think of (from U.S.D.A Prime to Wagyu) cooked to perfection. Don’t miss their amazing bread and ask for Genial General Manager Frank - who happens to be from Belfast - for some exceptional local knowledge.

Where to stay

Park Plaza Hotel: After a $100 million renovation, the refurbished Park Plaza - climbing 14 storeys with views of the public gardens and streetscape - is one of the busiest spots in Boston’s Back Bay. Its exceptional location sets it above its competition, while remaining reasonably priced. Prices from $189 per night. For more, visit bostonparkplaza.com

Boston Encore Harbor: A little bit of Vegas has launched in Boston, and it’s hard not to get swept up in the grandeur of this brand new hotel (pictured above). The Wynn Casino group opened its first east coast hotel in summer 2019 after a $2bn investment, boasting: 10 restaurants, a life-size floral carousel crafted using fresh flowers, and a 210,000 square foot casino. If you partake in one indulgence, make it a visit to the spa, which is a design mix between Versailles and Malibu with service to match. Prices start at $129 on weekdays. For more, visit encorebostonharbor.com.

Insider info

During our travels from Boston to Cape Cod, I insisted on a quick pit-stop to Plymouth, home to Plymouth Rock, said to be the first spot touched by the Mayflower boat hosting the pilgrims. The rock itself is protected in a secure case, but the town itself has all the New England charm you would expect of such a vestige in America’s history.

Cape Cod, Massachusetts

What to do

Cape Cod is expansive, with each small town possessing its own unique charm like Harwich, and Chatham (Hyannis and Falmouth are much larger). The scenery on this picturesque peninsula - home to the Kennedy Compound - fits its reputation as one of the most beautiful places in the United States. Beaches are plentiful, main streets are the stuff of movies and the people are as genuinely friendly as you would hope.

A car is essential around these parts and it gives you the most flexible access to exploring Cape Cod and its surrounds. Pay a visit to the Heritage Museums & Gardens (in Sandwich), a breathtaking 100 acres of carefully curated gardens, with a special focus on hydrangeas. Or walk along the The Knob (Woods Hole), which is often described as the most beautiful spot in Cape Cod. It’s the perfect spot to blow away the cobwebs - or in this case, jetlag.

Where to eat

Chatham Squire: A bar and restaurant divided into a venue for sit-down meals and another for a more raucous crowd after dark.

Corner Store Chatham: This unassuming shop fills up fast even after its 6:30am opening time, thanks to their famous breakfast burritos. If you sleep in, their regular burritos are also a knockout.

Where to stay

Wequasset Resort & Golf Club: There’s something distinctly Americana about staying in a golf club in Cape Cod, with a view overlooking the bay. The newly refurbished cottages invoke a sense of contemporary New England with white shutters and deep maple furnishings. Not to mention the fire pit outside every room for a cosy night in. Prices average at $600 per night. For more, see wequassett.com.

Insider info

If you do one thing while in Cape Cod, make it a drive to Provincetown, one of the most inclusive towns in all of America. Pride flags adorn the streets and nearly every home encapsulating a sense of wholesome splendour. And its beachside setting makes for a perfect backdrop. Try lobster arancini at The Lobster Pot and make sure you have time for some fried dough before the hour-long drive back to base.

Newport, Rhode Island

What to do

It’s hard to overstate just how impactful the Newport Mansions are - not only to the booming local tourism economy, but also on an inspiring scale of old monied Americans, like the Vanderbilts and Astors.

The Breakers is a summer “cottage” previously owned by the Vanderbilts (it is now run, as most are, by the local preservation society), and showcase the jaw-dropping splendour of last century’s early millionaires (tickets are $26).

Other show-stopping homes include The Elms and Marble House. For a more inclusive experience, visit the Newport Visitor Center and take part in a bus tour, which includes admission for the above and coastal views along the Ocean Drive; with celebrity mansion-spotting to boot ($36).

Take to the seas with a sunset harbour tour in a classic schooner by the Classic Cruises of Newport (average is $35), during which your guide will highlight historical landmarks and an alternative view of the estates, islands and lighthouses. It is, without question, one of my favourite cities I’ve ever had the pleasure of visiting.

Where to eat

Brick Alley Pub: A bustling bar on Thames Street featuring burgers, nachos, lobster and everything else you can think of on the menu. Top class service with a huge beer and wine menu.

The Chanler at Cliff Walk: For a meal of sheer indulgence, pay a visit to The Chanler at Cliff Walk - a luxury hotel in a league of its own at the epicentre of luxury hotels. The cafe serves Mediterranean-inspired classic New England menu for lunch and dinner year-round, and the food is only outdone by its panoramic view of the iconic cliff walk.

Desserts & Drinks: Delicious memories of the Cookie Jar’s sugar cookies still keep me up at night. And Sprinkles, which specialises in cupcakes, cookies and cakes is filled with a lengthy list of sweet treats which taste as good as they look. If you have time, stop by the Castle Inn for a sunset cocktail outside.

Where to stay

Hilltop Inn: When it comes to charming New England inns, the Hilltop is up there with the best. Centrally located in Newport’s Historic District, this five-room property has been lovingly restored to its original early 20th century glory. It’s a dreamy dichotomy of old world and new, with polished hardwood floors, original mouldings (and what I can only describe as a photogenic open staircase), and each room has a large modern bathroom, plasma TV - and ours had one of the most comfortable mattresses I’ve ever slept on. Prices range from $300-700 in the on season and off season is $100-$400. For more, visit hilltopnewport.com.

Insider info

For one of the best views in Newport, walk the 3.5 mile Cliff Walk, which borders the back lawn of the endless row of mansions. Even better? It's free of charge and offers an unparalleled view of some of the most jaw-dropping properties in the world.

New Haven, Connecticut

What to do

When you’re not tucking into a slice of pizza at one of New Haven’s many world-famous pizzerias, exploring the city on foot (and working off some off those mozzarella calories) is the best way to explore this compact city.

Yale University, the jewel in this Connecticut glistening’s crown, offers multiple daily guided tours across its expansive campus, dating back 300 years (tickets are $40). The tour involves a visit to the Beinecke Rare Book and Manuscript Library, an extraordinary six-storey glass building with “windows” made of translucent Vermont marble panels to protect its valuable contents. It’s a must-visit for any literary lover- and it also gives an opportunity to see one of the last remaining Gutenberg Bibles in person.

Where to eat

Frank Pepe’s: This might be the most famous pizza in the US - and with good reason. New Haven-style pizza, known to locals as ‘apizza’ is a thin crust, coal-fired type of pizza which is cooked a little longer and gives it a signature chew. Try their original tomato pizza and contrast with their white clam.

Modern Apizza: Another New Haven classic (Modern Appiza, Frank Pepe’s and Sally’s make up the New Haven Pizza triumvirate). Here, you can go off-piste with toppings a little more and the brick oven cooked pies are a triumph.

Where to stay

The Study at Yale: This brand-new property in the centre of New Haven overlooks Yale, and is the latest launch in the university-adjacent hotel branches, growing along the East Coast. The Heirloom restaurant features a contemporary New England menu utilising fresh, local ingredients like scallops, alongside duck breast and pumpkin caprese - with one hell of a cocktail menu. Prices from $270 per night. For more, visit thestudyatyale.com.

Insider info

New Haven is an unlikely central hub to larger cities like New York, Boston and Philadelphia, each just a few hours’ drive away by car, or by rail. Don’t rule it out as a base, or at least a one-night destination for your travels.

Portsmouth, New Hampshire

What to do

My first and only regret about visiting Portsmouth was that I only stayed for one night. This majestic seaside town has all of the comforts of a town with the amenities of a city, and was one of my favourite places I’ve ever visited Stateside.

To explore it by water, Portsmouth Harbor Cruise ($21) for a 90-minute narrated tour of the coast, with views of everything from lighthouses, beaches and a former naval prison. (Even Democratic presidential candidate Pete Buttigeig thought the same as he was campaigning there during our visit).

Stroll through the antique shops and art galleries for some locally-made products in every price range and the picturesque square is the closest you’ll find to a real-life set of the Gilmore Girls.

Where to eat

Raleigh Wine Bar + Eatery: This cosy wine bar tucked away downtown, was one of the most memorable meals of my entire life. From the peach toast on zucchini bread to the roast squash arugula and heirloom melons with pole beans; I’m still salivating at the thought and will make it my life’s travel mission to visit again.

Bennetts Sandwich Shop: An award-winning sandwich shop where the Italian Hero reigns supreme..even if you’re adventurous enough to try it for breakfast.

Where to stay

The Sailmaker’s House: This dreamy home away from home is a 10-room inn dates back to 1801, but a recent refurbishment means you experience that rich early American history with all the mod-cons you’d expect from a five-star hotel - in living colour. Bright colours carry through the house, alongside narrow stairways, slanted pine floors and original windows, and gardens. Prices start at $119-$399. For more information, visit sailmakershouse.com.

Insider info

Your must-see in Portsmouth is the Strawberry Banke ($19.50), an outdoor ‘living history’ museum which is home to historic houses, taverns and period gardens in some of the best preserved representations of early American history.

Portland, Maine

What to do

This coastal hub lives up to its reputation as Maine’s coolest city. It provides a reprieve from the picturesque New England towns with a rustic urban vibe - and plenty to see (and eat, but we’ll get to that in a minute).

The Old Port is home to a number of bars and restaurants, each with their own appeal. The micro-brewing industry is booming and the Maine Brew Bus lets visitors experience some of the best in town ($69.99) with a visit to two breweries and a winery. They also give guests one of Union Kitchen’s famous hand pies (a pastry made using biscuit style dough) and a quiz at the end to revitalise your competitive edge.

There are tours for everything here: a historic walking tour, lighthouse, coastal seafood, biking, museums - take your pick from this cultural mecca.

Where to eat

Becky’s Diner: A quintessential American diner experience that is not to be missed. Opening at 4am daily to feed the hungry local fisherman, this is a no nonsense place serving all day eats; but in particular, try the tuna melt.

The Highroller Lobster Co.: The title of best lobster roll is contested fiercely in Maine and The Highroller is consistently at the top (or near it) when award season rolls around. Expect lobster bisque, tacos, grilled cheese and of course their classic roll: all things lobster.

Duckfat: A small charming restaurant & sandwich shop focusing on produce cooked in their signature duck fat. Don’t miss their knockout poutine: Belgian fries topped with cheese curds, duck confit and gray with a fried duck egg on top.

Where to stay

The Danforth: Re-opening as Blind Tiger this month, this Danforth Street hotel is a few minutes’ walk from the action at the West End. Each of the nine rooms is the boutique hotel reflects a modern twist on the building Prohibition-era roots, with a speakeasy-turned-billiard room in the basement or the fourth-floor cupola with cityscape views. Prices start at $127 pp per night. For more, visit blindtigerportland.com.

Insider info

This is an obvious insider tip, but if you have an interest in drinking alcohol (and are of age), remember to bring your ID as it’s strictly enforced where alcohol served in the city. I haven’t looked under 21 for several years and I was ‘carded’ everywhere; especially if you want to visit a brewery and caution is particularly exercised.

Kennebunkport, Maine

What to do

The first thing that springs to mind when it comes to Kennebunkport is the President Bush Compound. The family have long-standing roots in the place and their island mansion island has become a must-see landmark for tourists - as have the Secret Service agents who are ever present in the surrounding area.

For a view of the world-famous mansions and a sailboat experience, try a two-hour sailing trip with the Pineapple Ketch ($45) where you can also spot some marine life. If you’re tired of walking around everywhere, it’s best explored by bike and there’s ample tours to choose from.

Where to eat

The Clam Shack: Perched at the bridge of the Kennebunk river, this scenic spot was the writer’s favourite lobster roll (of many) in New England. Sit on one of their benches devouring their simple yet immaculate lobster and watch the boats on the river. When they ask if you’d like 'mayo or butter’ your response is 'both'.

Rococo: This artisanal ice cream bar off the main street changes its menu regularly, but I can personally attest to the sweetness of their Maine whoopie pie and maple walnut flavours.

Where to stay

Cape Arundel Inn: To describe the Cape Arundel Inn as majestic would still be doing it a disservice. It’s considered to have one of the best views in the America (uncontested in New England) overlooking the Atlantic Ocean. Get lost with an evening of board games on the main house’s wraparound porch, with a cocktail in hand; or soak up the sun at its private pool located a few minutes’ walk away (and there’s a complimentary wine hour). Accommodation is available in the main house, club house of ivy cottage, meaning the choice is endless. The Ocean restaurant is a hit with locals and visitors alike and its expansive menu means there’s plenty of options to choose from. capearundelinn.com

Insider info

A sunset view in the home of sunset views means space is of the essence; which is why locals decamp to Parson’s Way, a beautiful spot to toast the end of the day and most importantly, free of charge.

How to get there

Caitlin flew as a guest of Aer Lingus, which currently operates twice daily flights from Dublin direct to Boston and a daily route from Shannon. Fares start from €199 each-way including taxes and charges, when booked as a return trip. For specifics, see aerlingus.com.

How to get around

Caitlin travelled as a guest with Hertz Corportation, one of the largest car rental companies in the world. For the best rates go to hertz.ie or, if you feel you need further assistance with a reservation, your local travel agent can advise you and place the booking for you (see hertz.com/usaroadtripplanner).

For more information on visiting New England, see discovernewengland.org