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    From Chicago to Maine: itinerary along the beaches and lakes of Illinois and New England

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    Joel Fulleda

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    Here is Daniela's journey, who has chosen a particular itinerary, deciding to combine the beauty of Chicago with the Maine coast, a winning combination as she herself defined it. Let's find out how this trip between Illinois and Maine took place, which included stops at numerous interesting and little-known beaches ... 

    26/7 - Departure: Milan - Amsterdam with Alitalia and then Amsterdam - Chicago, with a surprise upgrading in business: wow !! The flight passes by which is a pleasure, between food and sleep on the marvelous extendable armchairs on the second floor of the jumbo. Taxi to the Allerton Hotel on the Magnificent Mile, a 1922 brick building, a true landmark. After the shower we are very tired, but we take a turn towards the loop, outdoor dinner at Mc Cormick & Schmicks, overcast weather but not cold. The buildings around it distract us from the food… impressive!

    27/7 - Wake up at 6 for the time zone. At 11 we booked thearchitectural boat tour, but first we have an encore of French breakfast with savory croissants, croque monsieur, etc at “Toni's”. Super full, we get on the boat, luckily in the only sunny hour of the day. The coach explains the various styles of the skyscrapers, as well as a bit of the history of the city and its incredible development thanks to the river. We feel dizzy as we see the buildings reflected in the river and juxtaposed with each other in a highly effective mix of styles.

    After the boat tour we walk to the Millennium Park, to reflect in the huge mirror bean called "Cloud Gate" and to admire the giant metal structure of the Pritzer Pavillon theater. We return to the hotel along the State Street, the street glittering with lights from the theater signs. Shopping session on the Magnificient Mile to finish the day. We struggle to find a place to dine where there is no long queue (it's Saturday night). We end up in a pretentious steak house near the hotel where we drop $ 120 for two steaks.
    Magnificient Mile

    28/7 - The weather is overcast and very cold. I go out with fleece, jeans jacket and sleeveless down jacket and I'm not hot. Luckily today theArt Institute Museum. Arriving there we pass by Crown Fountain in the Millennium Park: two parallelepipeds about 15 m high facing each other, covered with LEDs with the faces of people who move their eyes and mouth and from which sprayed water sprays, where children have fun "wading" their feet. The museum is rich but no outstanding works. Many Monets, Renoir, some Van Gogh, El Greco, a Botticelli. The exhibition attached to the museum on fashion and impressionism is very beautiful.

    At the exit we are tired but luckily the sun comes out for the whole half hour in which we are lying on a bench in the park. After a snack at Prèt a Manger, walk around the loop to see the landmarks of the financial district. Here we see the square where the film ends Blues Brothers, the Rockery (brick) and the Chicago Board of Trade, in a narrow point called "Canyon". Let's not get on Willis tower for too long and the Merchant Mark is closed (Sunday!).

    We return to the hotel and leave in a hurry to go by taxi from Buddy Guys, a place famous for live music, temple of the blues. We can only get our wrist stamps and pay $ 10 each to get in, but there are no free tables. Moreover, the food that passes while everyone is waiting for the show discourages us. We should be up for a couple of hours… too much after the day! We then reluctantly decide to go and have dinner elsewhere. Four steps in the Loop and we come across "Exchequer”, A place that boasts the presence of Al Capone, with clippings from vintage newspapers and photos. We eat the best baby back rib of history, submerged in 2 cm of BBQ sauce that could have been avoided, but the meat is sublime. We spend $ 52 for two, including cheese cake.

    Buddy Guy’s

    29/7 - Finally good weather. We rent two bikes and ride on lakefront tr

    ail which is 23 km long. To the north. It is not hot but there is a beautiful clear sun. We meet wide and spotless beaches, some equipped, a gof court, tennis courts surrounded by parks. We stop for half an hour on the last beach to sunbathe. The lake impresses us: it looks like the sea, you can't see the opposite shore! Returned the bikes after 4 hours, we go to Navy Pier for a snack (very avoidable) and we console ourselves by queuing for 20 minutes for a 2 bowls Haagen Dazs for $ 6.

    Back at the hotel, we rest for half an hour but then the light is still too good and we go out to explore the northern part of Michigan Ave. We decide to invest $ 18 each to go up to the 94th floor of the Hancock Tower with the fastest elevator in the world: 94 floors in 40 seconds. Not recommended for otitis sufferers. The view from above is great and you still can't see the end of the lake. The light is beautiful and Chicago gives us the ultimate postcard view.

    Chicago Beaches

    We then have dinner at Weber's, a typical steak house, where we have to wait 30 minutes at the bar to sit down (we take advantage of it for a Pinot grigio and an appetizer), but in the end we eat an excellent skewer of very tender meat and excellent chicken.

    Useful information for visiting Chicago

    • What to see in Chicago
    • Where to sleep in Chicago
    • Chicago Pass: how to save on attractions

    30/7 - Today we leave. The sun helps us wake up early. Breakfast behind the hotel (the best, if we had discovered it earlier….). Then, after settling the bill, taxi to the airport. Upon arrival in Boston, the sun welcomes us with "scattered clouds" (as the captain says upon landing). It's finally a bit hot. I will no longer use the battery from here on out. Our red Chevrolet Cruze eats our suitcases and sets off in the direction Kennebunkport, our first stop in New England, where golden light floods the most picturesque, elegant and colorful village in Maine. Our motel a Cape Porpoise it is very basic but clean and has a beautiful lawn with a huge tree in front of it. Dinner in Cape Porpoise from Pier 77, walking distance from the motel, overlooking the lighthouse and the small lagoon. We finally eat fish and salad.

    31/7 - Today we go to the beach: Grooch's at Kennebunkport. Very large, very beautiful, very popular WASP (White Anglo-Saxon Protestant) Very large, flat that looks fake, it stretches 1 mile blind in front of elegant style mansions. Beautiful and rich elderly couples stroll, while equally beautiful and rich families play among the surf and umbrellas. The sun beats down and the tan will testify, but you don't feel it because there is a light breeze and the air is warm but not beyond comfort.

    Lunch in a small and mediocre store, the HB Provision: an emporium where you shop for food and can also be consumed on the spot, among wooden shelves and smells from Old America. Two salads. Afternoon with an ocean front walk to the Bush villa, a tourist pilgrimage destination for curious people like us. Evening in search of two seats at the table in a restaurant that we like; after an hour of running, book, enter, exit, look and smell…. let's go back to Cape Porpoise, to the Captain's. And here, in a simple and semi-home environment, we enjoy a seared tuna and a very good Haddock.

    Kennebunk Beaches

    1/8 - Let's go towards Boothbay, our next stop. Two stops await us on the road: the first is there Old Orchard Beach, a long and sometimes crowded beach, with a Riccione-like environment, very popular with Quebequensi. There is a wonderful time, we even manage to do a "puccio" in the ocean. We arrive at Boothbay Harbour around 19, as we got a bit lost around Portland, which makes a bad impression on us. The Harborage Inn booked is very nice and Jennifer is a knowledgeable host. Dinner at Seagull's, one of the restaurants overlooking the wooden square in the center of BBH. Both the tuna with sesame and the mixed grill are excellent. A musical ensemble brightens up the environment by warming up the colorful group of local friends.

    2/8 - Overcast skies, drizzle at times. You go to visit Damariscotta, not far away. Nice Main Street, where we eat a good light lunch with hot sandwiches and nice salads. Then you go to Pemaquid, fascinating place for the horizontal cliff and the lighthouse, which we visit inside (do not miss our article on the lighthouses of Maine and New England). The sun drives away the mist and after a few photos we go to Pemaquid Beach, beautiful and deserted. We would stay longer, magical atmosphere, but we come away so as not to miss the Opera House, where we booked for the evening two tickets for the concert of the “Cherish the Ladies”, a singing group of Irish origins. Dinner - excellent - on the terrace of the Boathouse, overlooking the harbor at sunset. Noteworthy are the crab cakes and craft beer.

    Pemaquid Beach

    At 7,59 we enter theOpera House, historic building (National Monument) from 1901, already full of spectators. After the opening of a musician (acoustic guitar, a kind of Irish banjo) the stars of the evening enter, all women (6). We do not understand everything but they seem nice, with the leader of NY, daughter of Irish, as wide as a newsstand and virtuoso of pipe and flute. Fun music and amazing dances. Funny and good. After theater with a walk and waffles on the harbor.

    3/8 - Time opens up to beauty and we decide to dedicate the day to sport. Two-seater kayak in the morning, one hour in the harbor. We would like to take the bikes but they are broken, we go to the other bike rental in Boothbay Harbor and we leave with one too small and the other braking. We pedal towards Hedick’s Lightouse and Beach but the road is dangerous and after a while we give up. Back at our Inn we allow ourselves some sun by the sea on a very comfortable one Adirondakee chair. Dinner over the pedestrian bridge over the harbor, across the bay from the Lobster Dock, overlooking the bay, where for $ 50 we get a whole lobster with corn on the cob, two excellent crab cakes and a plate of scallops au gratin. All great! The lobsters are boiled alive in a cob retina by a team of Bulgarian boys one step away from us. It's kind of impressive, better to eat than watch (also read our Maine Lobster Tour).

    4/8 - We leave under a beautiful sun. First step Camden, the "Portofino" of Maine. Two steps along the port and…. Street! We get on a "Windjammer", a sailing ship reproducing the ancient ones, which takes us off the bay for two hours. The weather is wonderful, we enjoy it. Then a quick snack on the marina (focaccia) and we continue the journey.


    We arrive at Bar Harbor around 19. We settle at the White Columns Inn (booked by spain, like all the others) former church with large white columns at the entrance. We have the Hare Forest room, super Victorian, with a very high four-poster bed and full of white lace ruffles. Going out for dinner, we are struck by the large number of tourist shops and the spectacle of the sunset over the bay, with many small islands in front. In some ways it may recall a Norwegian landscape, but the houses are few on the banks and all in Victorian-style wood. We have dinner at "Gelyn's" - salmon - on Main Street and we also manage to take a stroll around the shops that strangely close late, at 22 or 23 pm, then we climb the hard bed.

    5/8 - We wake up with a beautiful sun ready for Acadia Park. We don't like breakfast (bacon quiche and plum cake slice in the same dish) but alas you can't choose. Acadia is a huge wood on the same island as Bar Harbor, la Mount Desert Island, with sheer cliffs of granite, strangely square in shape. We drive the Loop and stop for an hour in the only one Sand Beach. We resist lying down even if the sun comes and goes and it's all a put on and take off the golf, while the fearless even take a bath. Then the sky opens, we decide to stretch our legs on the path that starts from the end of the beach and arrives after a loop of about 30 minutes on the other side.

    Sand Beach ad Acadia National Park

    Nothing special, but at least we moved a little. We finish the tour of the park by car, stopping at the top of the Mount Cadillac and for some photos from above to the islets in front of us and the cliffs, but overall this park seems inferior to expectations. Certainly it strikes such dense vegetation on an island so far north and with such jagged contours. After a quick shower, we go to the Marina to walk the Shore Path, a path built in the late 1800s that runs along the bay for about 1 km. Beautiful sunset over the bay !! In the end we are very hungry because today we ate only Maine strawberries and blueberries bought along the road outside Boothbay. We have dinner at "Cafè This Way": two excellent tuna, but mine is a bit too spicy. Here they can't resist covering all the best flavors with sauces and spices. After dinner we can go for a walk and even a little shopping.

    6/8 - Beautiful weather today. Too bad having to drive, but New Hampshire and yours awaits us Golden Pond, about 450 km from here. The road is long, but most of all it is slow, with the maximum limit on the highway set at 65 miles, at best. We knew it and we take it easy. Lunch is at Governor's, perhaps the worst place we have eaten so far, on the other hand all the photos of the Governors of Maine from the 800s to the 70s hang on the walls. We leave and cross beautiful forest landscapes under blue and cobalt blue skies to the lakes region, in particular the Sebago lake, little considered by the Lonely Planet but beautiful, especially in the golden light of this afternoon.

    We stop at Naples, where we rent what we thought was a pedal boat and which turns out to be the slowest boat on the planet! We also experience the thrill of taking off a seaplane 10 meters from us. Still other km in the middle of almost uninhabited forests and finally we arrive at Holderness! Beautiful, beautiful lago Squam reveals itself in the trees. And here we are at our "Inn ON Golden Pond" and our beautiful "Owl's nest" room. Dinner at Walter's Basin, the babyback rib and Piero's NY sirloin with blue cheese are discreet.

    Squam Lake

    7/8 - Under an overcast sky we enjoy Bonnie's nice and good breakfast: toast, rhubarb jam and a splendid blueberry pancakes. Yummy, the best breakfast of the holiday. A shy sun invites us to look for the Squam Lake Association to rent a two-seater kayak and venture out on the waters of Squam Lake. Beautiful scenery, a lake larger than we expected and the sun now full, we even attempt a clandestine ditching on a small beach reserved for residents of Holderness, from which the Beach Attendant after 30 seconds flat kindly chases us.

    In the afternoon we rest on the public beach of Little Squam Lake, where they are happy to welcome us for $ 2 each. Back in the village (it can't even be called a village) we enjoy a slice of excellent raspberry and rhubarb pie and return to our Inn. For the evening we decide to visit Meredith, 6 km from us, on the lake Winnipausakee, the largest in the area. The place says little, in US holiday style, but we come to Giuseppe's for dinner, where the staff proudly illustrates the Italian origins of the founding family and where we risk a pizza and spaghetti with mushrooms, surprisingly good. It will be boredom for the usual US food, but we seem to have eaten very well, including the tiramisu and final cannoli. Short walk on the lake to work off and back to the Inn sated.

    8/8 - Today we leave. We have decided to leave out the Vermont and return instead for the last two days of vacation on the coast, even if we have not booked the overnight stay. Breakfast with sweet French toast and chat with Bonnie, with her travel memories visiting friends from Biella. Along the way stop at Concord, capital of New Hampshire. After wandering around Portsmouth, a town in the very few kilometers of the NH coast, where we thought to stay overnight, but which we found horrible to say the least, we headed straight to Ogunquit, knowing full well it was Friday night and it would be hard to find a place to sleep two nights, but in my memories of the previous trip it was worth it. And it is a confirmation! After unsuccessful attempts elsewhere, we find a great room at a decent price in the same hotel as last time, The Meadowmere Resort. The first evening we have dinner in a delightful place in Perkins Cove, on a terrace overlooking the sea. We enjoy it! The temperature in Ogunquit is perfect and even the village - as I remembered - absolutely deserves it.

    Ogunquit beach

    9/8 - Today, last day, the program includes a shopping tour in the outlets of Kittery, not far from here. Never could the program have been more appropriate: today IT DILUVIA! And it will rain all day, so we have the excuse to spend the day around the outlets, where we buy a little bit of everything. Let's go back to Ogunquit at sunset, just in time to take a trip to the beach to enjoy the spectacle of the sky opening and the sun setting with a bright light on the long semi-deserted beach…. Stupendous. This image will remain in our eyes.

    For our last dinner of the holiday we choose a place not far from the hotel, where we do a lot of waiting before having a table but we have dinner with excellent meat in the only place WITH TABLECLOTH of the whole holiday. A luxury. After dinner, stroll through the little shops, open until after 22pm (a rarity).

    10/8 - Today alas we are back. The flight is from Boston around 18 pm. We take advantage of the splendid sun to spend a few hours on the beach. It is a marvel: deep and endless beach, clear sand, calm sea, brazen light. Most of the people are concentrated towards the ground, thus leaving a huge deserted space of about 100m. on the water's edge. We position ourselves with our towels in a very little crowded spot on the beach. After about half an hour we understand why they were all piled high… .. the tide suddenly rises and a nice long wave sends us soaking towels, creams and shoes! Patience, we won't need them any more tomorrow. We move back and still enjoy the last hour of Maine beach. A drive to Boston with the anxiety of missing the plane due to traffic and we are ready for the return flight.

    Other useful resources

    If you are thinking of embarking on a New England itinerary, I would like to point out some resources that may be useful for planning your trip.

    • Our guide on how to plan a tour of New England.
    • Our tips on Country Inn: the best Bed & Breakfasts in the region.
    • All you need to know about Acadia National Park, New England's most fascinating natural park.
    • Our advice on the city of Boston, a reference point for visiting the region.
    • Our section with all the recommended itineraries in New England.
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