I’m not sure what it is about the words ‘road trip’ that makes me so excited. Perhaps it’s the spontaneity of it, the feeling that anything could happen and that any moment now you’re going to come across a gem of a place you never would have known about. Whatever it is, when I put it to my two friends that we should see some of America’s East Coast, they jumped at the chance and we decided when better to go than October for ‘leaf peeping’ season (as it’s known – due to the vibrant fall leaves).
I read many, MANY forums and scoured maps to see what we could cram in during our 10 nights away, and the best route to take. We wanted to see the Hamptons and Cape Cod, so decided that we’d fly into Boston and out of New York, giving us the chance to go both up and down the coast. Flights were pretty cheap at around £320 each with British Airways, as we booked almost a year in advance and, with that done, we started looking at spots to stay and visit. We only had 10 nights, so it was always going to be a whistle stop tour, but here’s how we broke it down, where we stayed and what we discovered…
Day 1 & 2: Boston
I wasn’t sure what to expect from Boston. We’d pre-booked two nights at the Marriott Copley Place, which was ideally situated for us to walk around the city and as we arrived in the afternoon we thought we’d get straight out and explore. We walked so much – through Boston common, around Beacon Hill (my favourite part – the Victorian brick row houses, hilly streets lined with autumn displays and scattering of trendy boutiques, cafes and antique shops are a must-see), and along Newbury Street where we treated ourselves to pedicures after a long afternoon of walking! We went for a drink in the Cheers bar (well, you can’t visit Boston and not , can you?) and had an amazing Mexican meal at Lolita in Back Bay, near to our hotel (where they brought us out grapefruit ice to start, which they poured tequila over!).
The second day, we did more walking. Honestly, our feet hurt so much after those first few days but it was totally worth it, especially as the sun was shining. We considered the hop on/hop off bus, but it felt so much better knowing we were burning some calories and being able to explore on foot. This time we took in the wharfs, the Boston tea party ship and Quincy market.
There’s lots more to do if you have time and you’re interested in history, such as The Freedom Trail. We read up a lot about everything but really enjoyed walking around ourselves.
Foodie Tip: Visit Tatte cafe for the best coffee and pastries, and The Friendly Toast for a quirky and totally Instagramable breakfast spot.
Day 3: Salem, Rockport & Portland, Maine
We picked our car up the next morning from Avis and started our trip along the coast, with our first stop in Salem, Massachusetts. This small but very pretty town is famous for its 1692 witch trials, during which a few locals were executed for allegedly practicing witchcraft. Being it was October, the town was already getting ready for Halloween, with decorations, markets, and the usual ghost tours and haunting walking tours. Despite its very obvious touristy focus, we liked the town’s feel, with quaint shops and waterfront walk.
The next stop that day was Rockport, however, we hadn’t timed it that well as it was not only coming out of the tourist season, but it was also Colombus Day (a public holiday), which meant most things were closed. We stopped for a bite to eat, admired the beach and cute waterfront houses and then it was on to Portland, where we’d booked the Westin Portland Harborview.
We all loved Portland. Its cobbled streets, one-off shops in Old Port and the amazing seafood restaurants gave it a real charm and it’s really easy to walk around. We ate at DiMillo’s On The Water – a floating restaurant with views over the harbour and each of us tried a different lobster dish (the lobster stew won out!).
Sightseeing Tip: Portland Head Light is the oldest lighthouse in Maine and is set on a head of land with breathtaking views. We visited it before we set off for Stowe and were really glad we did. There’s lots of lighthouses along this stretch of coast, but this one’s a real beauty.
Day 4 & 5: Stowe, Vermont
Stowe is predominantly a ski town in the mountains – it’s not huge but it’s affluent, it’s pretty and most of all, there’s stuff going on all year round. The drive there from Maine takes around four hours, but boy was it worth it. We checked in to Spruce Peak, a luxury resort that’s part of a whole village, with bars, restaurants and separate lodges. In the winter it has a gondola straight to the top of the mountain and I can only imagine what a great place it would be for skiers. That said, visiting in autumn didn’t disappoint. We oohed and aahed at our room, with its balcony overlooking the mountains that were rich in all their vibrant red and orange leafage, and began making plans for the next two days.
Kayaking was a must on our list, so we rented some from a local hire shop and the guys there took us to the Waterbury reservois. Out there on the water, with nothing around but the mountains, I don’t think I’ve ever felt quite so remote and surrounded by nature. There was a real stillness to it, but at the same time, lots of small movement from wildlife – birds, moose and bears are all common to these spots (although we were reassured they are black bears, which are a little less aggressive than those brown ones apparently!).
We had dinner at Solstice the first night, which is the AAA four diamond eatery at Spruce Peak lodge, while on the second night we went to the Whip and had the best red curry stir-fry – can’t recommend this place enough.
On our second day we hired bikes from MountainOps, which is just down the road from where we were staying, and cycled along the bike track that takes you all the way into Stowe town, following alongside the river. If you want an easy, but beautiful cycle, then this is for you, as it’s mainly flat, around five miles long and passes through woods, corn fields and next to bubbling brooks. Just don’t forget bike locks so you can have a look around the town (you can park in the church car park), and stop for something to eat and drink before cycling back.
Evening Tip: Go for a late-night soak in the outdoor hot tubs at Spruce Peak, with a glass of champers and the mountains as your view, before keeping toasty round their fire pits – you might want to treat yourself to one of the Sch’mores kits they sell in the on-site shop, too!
Day 6: Fairlee, Vermont
Fairlee was an overnight stop for us, to break up the journey from Stowe to Cape Cod. We stayed in this Airbnb and arrived fairly late, so didn’t get to see a lot of what it had to offer, but if you’re looking for a quirky setting to lay your head, then this one’s a goodie. Harrison, who owns the house, told us that he’d built it and the views are breathtaking, with large glass floor-to-ceiling windows out towards the lake below. We had the upstairs floor to the house, which has a bedroom (plus another double bed on a mezzanine), roll-top bath, WC and small kitchen – oh and did I mention the outside deck, complete with hot tub?
Foodie Tip: For an asian-inspired menu with a twist, try Samurai Soul Food. It’s not glam in any way, but the food was good.
Day 7 & 8: Falmouth, Cape Cod
We were up early to get to Cape Cod and another Airbnb, this time in Falmouth, where we rented a little coastal cottage all to ourselves. Cape Cod is a mixture of lighthouses, quaint villages, great seafood and beautiful beaches. In the summer, you can whale watch and enjoy the beaches, but for us, it was more about exploring as much as we could in our limited time here. Our Airbnb was about 10 minutes from Falmouth town, so on our first evening we decided to get an Uber there and back so we could all enjoy a meal and drinks after at Liam McGuire’s Irish Pub. Live music, a buzzing bar and friendly locals make it a good hotspot and it was a late one for us.
We’d already explored the town, with its splattering of tourist shops and quaint eateries, so the next day we drove to Woods Hole (three miles away from Falmouth), parked up and got the ferry over to Martha’s Vineyard for the day. Now as a Jaws fan, seeing the place where it was filmed was a highlight for me and you can still see some of the locations featured in the film. You’ll also see shark warnings on the beaches, as the great whites still frequent these beaches on occasion.
There are a couple of different towns on Martha’s Vineyard that you can get the ferry to, but we decided on Oaks Bluff, as we were keen to see the gingerbread houses – a set of 300 colourful Victorian cottages that are reminiscent of the of the gingerbread house in Hansel & Gretal, hence the name. This small village actually started off as a 19th-century Methodist campground and today they make a pretty tourist attraction. If you do go, make sure you have a quick walk around – you don’t have to spend long, but they’re well worth a look.
Then it was off to explore some more of the island. We hired bikes (there’s a bike rental place right by the ferry) and cycled to Edgartown, a fabulous mix of old-world charm and harbour-front restaurants and small shops, where we had lunch, before cycling back and looking in all the little touristy shops (well, I did need a Jaws t-shirt after all!)! Then it was on to the ferry for the 45-minute crossing back to Falmouth.
Foodie Tip: If you want some good seafood, then you can’t beat dinner at The Flying Bridge in Falmouth, with its views over the harbour and out to Martha’s Vineyard. It made the perfect setting for our last night on the Cape.
Day 9 Rhode Island
When I was looking for hotels in Newport, Rhode Island, I couldn’t resist the Jailhouse Inn, which was built in 1772 and, as the name suggests, used to be the local jail. Today it has 23 beautifully decorated bedrooms and made a good central point for us as tourists.
We walked a LOT here the day we arrived, including the famous three-mile cliff-top walk, which takes you along the oceanfront and passes by the backyards of the Newport mansions – ‘summer houses’ built for the obscenely rich back in the 19th century. You don’t have to do the whole three miles, as there are entrances/exits in a few places along the walk, but the scenery is incredible and you almost can’t believe you’re in a city.
On our way back, we passed a small festival that had Newport buzzing and ended up having drinks in a bar nearby. The perfect way to end a day full of exercise and rest our tired feet!
Drinks Tip: Fancy a drink in America’s oldest tavern? You’ll find the White Horse Tavern directly across from the Jailhouse Inn.
Day 10 & 11: Mystic & New York
The final leg of our road trip took us to New York, but we thought we’d stop off en route in Mystic, a historic coastal village in Connecticut. Those that have seen the film Mystic Pizza and others located on the Mystic River might recognise parts of it, and if you’re looking for the most picture-perfect setting to fall in love with, then this is it people. We stopped for coffee at Sift, a family-owned, French-inspired place owned by pastry chef Adam Young, winner of Food Network’s 2018’s Best Baker in America award. And yes, there is an actual shop named Mystic Pizza, which was the inspiration for the film.
Travel Tip: Take route 1 for a much more scenic road than the freeway.
Having decided not to drive all the way into New York (many had suggested dropping the car off earlier when I was researching the trip on forums), we handed it back in New Rochelle and caught a train from there to Grand Central in New York, which worked out at about £14 each. From there we walked the five minutes to our hotel for the night, the Cambria, Times Square – chosen for its central location.
Dinner that night was ribs at a local restaurant, then drinks at Spyglass Rooftop Bar to toast the last night of our trip.
Our final day was spent walking around Greenwich and Lower East, before catching our flight home later that night. We loved every minute of our trip, but the highlights for me were Cape Cod, Maine and Vermont – all places I’d like to go back to and explore more at some point. That’s the great thing about a road trip, it gives you a taste of what places are like and keeps things interesting, with different sights in each stop. Now it’s time to plan the next one…!
