New England Fall – Adirondacks from Maine to New York

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New England Fall – Adirondacks from Maine to New York

There may be no better place to spend fall than in New England. The colors are legendary, the weather is crisp but not too cold, and the apple cider is flowing. This two week trip starts in lovely coastal Maine, crosses the White Mountains in New Hampshire to beautiful Stowe and Burlington, Vermont before heading to Lake Placid in the Adirondack mountains in upstate New York before winding down to the Catskills and the mansions of the Hudson River Valley. If you want fall colors (which we highly recommend) realize that it will be peak season and advance reservations are highly recommended/mandatory. The best time to visit is the first two weeks of October. Previously a week earlier might have been advised but global warming has shifted this a bit in recent years. Visit Fall Foliage tracker for help planning.

Length: 13 days

Transportation: This is a car based trip.

Recommended Guidebook: Moon New York State; Fodor’s New England

Day 1 – Portland

Day 2 – Freeport, Brunswick, Camden

Day 3 – Kennebunk and Ogunquit

Day 4 – Kancamagnus Highway, Franconia Notch, and Bethlehem

Day 5 – Montpelier and Stowe

Day 6 – Burlington

Day 7 – Fort Ticonderoga and Lake Placid

Day 8 – Lake Placid and the Adirondacks

Day 9 – Olana and Rhinebeck

Day 10 – New Pfalz and Awosing Falls

Day 11 – Vanderbilt Mansion, Old Rhinebeck Aerodrome to Tarrytown

Day 12 – Lyndhurst, Sleepy Hollow

Day 13 – Fly Home

  • Drive to Newark International Airport (about 1h drive)
  • Fly home

Detailed Itinerary

This trip is leaf peeping in New England’s greatest hits. There are a lot of other great places in New England you could visit – including Connecticut, more of Vermont, New Hampshire, Massachusetts, and Rhode Island but with the foliage this is a great opportunity to take in some fall colors and see beautiful upstate New York as well. We are suggesting starting in the north and heading south as that tracks the foliage – and things really start to close down in Maine after Columbus day. In planning, check that the site you want is open on the day you’ll be there.

Day 1 – Portland

Arrive at the Portland Airport and pick up your rental car.Check for prices and be sure to check on a drop off in Newark or New York.If the cost is too much you can return from Tarrytown to Portland to drop the car but that makes for a long (5 hours) and not very interesting drive at the end.

Depending on when you arrive, you may land in the evening, in which case take the time to wander the charming city at night. If you arrive earlier, reduce your itinerary by a day, or spend your extra day to simply enjoy wandering Portland.

Portland itself is Maine’s largest city, but it feels more like a charming and funky town. It has an amazing food scene, many local artists and shops, and an incredible number of breweries. Treat yourself to at least one full day to explore.

In terms of hotels, we have found the AC Marriott to be lovely and in the perfect, walkable location to everything you’ll want to see. The Press Hotel has a more boutique feel and located in an old newspaper building. Another good option is The Francis located in a historic mansion.

For dinner, head to one of our three favorites: Eventide Oyster Co, Fore Street, or Duckfat, though many restaurants are great and we list other options here. For dessert, head to local ice cream shop Mount Desert Ice Cream or get a drink an artisan cocktail at Blythe and Burrows or Portland Hunt and Alpine Club.

Day 2 – Freeport, Brunswick, Camden

Try to get an early start today as you have a lot to see. Today if you want to try another Portland coffee option, head to Tandem Coffee Roasters or Hilltop Coffee Shop before winding your way slowly up the coast.

Head north to lovely Camden and Penobscot Bay. We recommend the easy almost 2 hour drive to Camden, spending the rest of your day working your way back to Portland.

In Camden, if you are here before Columbus day you can reserve a sail on a tall ship on Penobscot bay – if you come much later the boats get wrapped up (literally) for the winter. We suggest booking your sail in advance. Before or after, park and stroll around lovely Camden. There’s lovely little park, fun shops, and lovely historic houses. A little further north (about a 10 min drive) you can drive up to Camden Hills State Park for a great view. After your morning sail, get lunch at Long Grain, Waterfront Restaurant, or Peter Ott’s on the Water.

Camden Harbor

After lunch climb back in the car and take a short drive to the Rockland Breakwater Lighthouse (16m drive), one of our favorite lighthouses in the world. You will walk out along a mile-long jetty into the sea where the lighthouse is situated. Fair warning, do not do this if the weather is bad or the waves are high as you’ll get fully drenched (we say this from personal experience).

We also recommend to be sure and save time for the Farnsworth Art Museum (10m drive) with a great collection on Maine artists and highlighting Andrew Wyeth but also his father and son, who were also artists. From here, it’s a short drive to Owls Head State Park and lighthouse (16m drive) situated on a bluff near the ocean in a nice forest park. Your final lighthouse of the day is thePemaquid Point Lighthouse where you can walk along the craggy rocks below and on sunny days head up the lighthouse tower (1h drive).

Rockland Breakwater lighthouse

Next, hop off the highway in Brunswick and you can drive by or wander on foot the leafy and attractive Bowdoin College (1h drive).

From here it’s just a few minutes to Freeport, where there are several outlet stores, most importantly the enormous LL Bean “mothership” spread over several buildings. The whole complex is really pretty impressive and a good place to pick up equipment for your next outdoor adventure if needed. Of note the store is open 24 hours (you never know when you might need a tent at 2am after all).Maine Beer Co. is also located in Freeport. The tasting room is spacious and bright, the beer is plentiful and good, and the woodfire pizzas they serve up are hard to beat. However you’re also right near arguably one of the best lobster shacks in the state,The Harraseeket Lunch and Lobster Company. Pizza or lobster…not an easy choice.

If it’s dinner time by the time you reach Freeport, grab dinner at one of the places just mentioned. If not, head back 20 minutes to Portland and have dinner atFore Street,or choose one from our list of Recommended Portland Eateries.

Grab after dinner drinks at the Portland Hunt and Alpine Club.

Day 3 – Kennebunk and Oqunquit

We start our day today with some Portland attractions before heading south to some beautiful beaches and a beautiful lighthouse.

Start with breakfast at Standard Baking Company, Holy Donut, Bard Coffee or visit the Portland Farmer’s market and grab something there. Portland has three main sites you can go in to visit: the Victoria Mansion, the Portland Museum of Art, and the Wadsworth-Longfellow House. Choose what sounds most interesting to you. For lunch, you can walk along the railroad track and well-marked path to the Eastern Promenade, a large riverside park topped with pretty mansions and large swaths of grass where you can sit and munch a food truck meal that lines up there for lunch as you watch boats sail by.

After that head south to York where you can see a series of historic York Museum Houses (47m drive). Or just head to lovely York Beach, a long sandy beach with pretty vacation homes. From here take a short drive to the Nubble Lighthouse (7m).

Continue on to Ogunquit. Another artist colony, Ogunquit is full of beachside resorts along sprawling beaches. If youhaven’t had lunch yet, Crooked Pine is a good option. Visit Ogunquit Beach which offers 3.5 miles of soft sand. It’s a good place to swim if you’re so inclined and lovely to walk along if you are not. Next head to Marginal Way which is a spectacular cliff walk. Along the 1.25 paved path are benches and stairs down to sea. Finish at M.C. Perkins Cove for a drink with a view or snack.

York Beach
Nubble lighthouse

Next drive down to the Kennebunks. This town is quintessential coastal Maine, set on the water with lobster shacks abutting fine arts galleries, historic mansion, and sand beaches. Start your time by wandering through the many galleries. The History Center of Kennebunkport also offers a self-guided walking tour map of historic homes which you can pick up. If you’re feeling historical walk to St. Anthony’s Franciscan Monastery with pretty serene grounds you can wander.Some fun shops to poke around in include Daytrip Society, Farm + Table, and Minka. Finish your time with a walk along Goose Rocks Beach offering soft white sand.

For dinner, we can’t recommend Earth enough (you must make reservations). After a great dinner time to head back to Portland (35m drive).

Day 4 – Kancamagnus Highway, Franconia Notch, and Bethlehem

The Kancamagus Highway was one of the first designated scenic highways and traverses the White Mountains of New Hampshire. It offers 34.5 miles of trails with scenic views. In fall, it is a really spectacular drive. It’s also popular so you may have some trouble finding parking at some of the more popular stops. We recommend getting started a bit early if possible for that reason.

First, drive to Conway (1h24m drive), then take the Kancamagus Highway (route 112). At each site we recommend parking and walking to see the site. Some sites you may have more difficulty parking, but each is worth the wait. First you’ll first come to the Albany covered bridge where it’s a quick walk to see the bridge. Next you’ll come to the Rocky Gorge where it’s a short walk to the gorge area then you’ll cross a footbridge to get to Fall’s Pond which is quite pretty with the fall foliage. Consider a stop at Sabbaday Falls and a 1.2 mile round trip walk to see the falls. Next you’ll hit some scenic overlooks, first Sugar Hill overlook and then three in short succession as you get to the crest. There are also several picnic areas – at Sabbaday falls and Otter Rocks so this may a good day for a picnic. As you reach the far end of the highway, you will pass Loon Mountain resort ski area. From Lincoln, where the Kancamagus highway reaches interstate 35, it is just a short 8 min drive to Flume Gorge in Franconia Notch State park. This is a popular hike so get reservations ahead online. Plan for about a 45 minute 2 mile walk through some very pretty fall colors and mountain scenery.

Albany Covered Bridge
Rocky Gorge

From the Flume Gorge drive to Bethlehem (20m drive) and check into your lodging atAdair Country Inn and Restaurant.

Grab pre-dinner drinks at Rek-Lis Brewing Company and have dinner at your inn.

Day 5 – Montpelier and Stowe

Have breakfast at the inn, and then head out to Montpelier (1h13m drive). Montpelier is the capitol of Vermont and a small but pretty city. Very closeby is Morse Farms maple sugar works where you can watch a video about how maple syrup is produced (short and worthwhile) and grab some maple syrup and maple ice cream.

From here, head toward Stowe. On the way, turn off for the Von Trapp Family Lodge. The Sound of Music Von Trapps settled here after fleeing Austria and built this mountain retreat. Just down the hill from the lodge is the Von Trapp Brewery where you can grab a beer and lunch.

View from Van Trapp Lodge area

From here it is about a 10 minute drive to pretty little Stowe. You might want to enter Gold Broke Covered Bridge for a scenic detour on the way there or back.If you’re a big beer aficionado, you can also stop by The Alchemist in Stowe which also has unique beers.

From Stowe towards Burlington, stop by the Cold Hollow Cider Mill for amazing apple cider donuts (20m drive). As if there has not yet been enough sugar in your day, also be sure to make time to stop by the Ben & Jerry’s Factory for a tasting, tour, and a visit to the flavor graveyard.

Then make the short (37m) drive to Burlington where you will check into your hotel,Hotel Vermont. If that’s booked, you can also consider The Essex Resort and Spa which is lovely but outside of town. Grab a pre-dinner drink at Misery Loves Company or your dinner spot,Hen of the Wood. We highly recommend getting reservations far in advance and be sure not to miss eating here.

Day 6 – Burlington

Burlington is a pleasant city situated on the shores of pretty Lake Champlain. There is a lovely path on the bluffs above the lake and a pedestrian-only street named Church Street with nice shops and restaurants. The University of Vermont, one of the oldest universities in the country (founded in 1781) has a lovely campus you can wander just a 15 minute walk (or 3 minute drive) up the hill from downtown.

For breakfast or brunch head to August First, The Friendly Toast or Blue Northeast Kitchen.

After brunch drive to nearby Shelburne Museum (34m drive).This fascinating museum is full of buildings transported from all over Vermont, a full size Paddlewheel steamer that used to ply nearby Lake Champlain, a truly remarkable carved circus parade in a specially built building that is an exact replica of the 2 mile-long processions that used to come into towns with the circus. The museum is also an art gallery with some truly stunning impressionist paintings and Americana painting and collections – it includes everything from coin operated toys to hunting decoys. It’s worth a half a day. After the museum, stop by Fiddlehead Brewing Co for more Maine beer.

Amish Round Barn at Shelburne Museum

Spend your afternoon wandering Burlington. Stop for ice cream at Scouts and Company.

For dinner try Juniper or Farmhouse Tap and Grill, or Farmers and Foragers food truck.

Day 7 – Fort Ticonderoga and Lake Placid

Have breakfast at Penny Cluse which is something of a Burlington institution. It’s not open every day so plan accordingly. If you can’t get in there, try Pingala Café (vegan) or Onyx Tonics (predominantly coffee).

After eating head out to Fort Ticonderoga (1h26m drive). The fort is very historic, at times was French, English, and American, and it saw action in the French and Indian War and American Revolution. It’s prettily situated at the south end of Lake Champlain and there are living history exhibits at the fort.

From here it’s a very pretty drive to Lake Placid, and though there are several nice roads you can take to get there, we recommend heading to High Falls Gorge, and the road will wind you along a lovely river under the face of Whiteface Mountain (the alpine venue for the winter olympic ski races in years past Olympics). You can actually take a cable car or drive to the top if it’s open. The High Falls Gorge is somewhat similar to Flume Gorge and a bit pricey, so decide whether you want to visit. It is very pretty and a nice leg stretch your legs after your drive.

Along the road to Lake Placid

Check into your lodging atHigh Peaks Resort. Other lodging options include Lake Placid Lodge or Mirror Lake Inn Resort and Spa.

For dinner tonight we suggest reservations at Kanu,

  • Maggie’s Pub, Great Adirondack Brewing Company
    • , Generations Tap & Grill, or Artisans. Pick one and make a reservation ahead of time.

    Day 8 – Lake Placid and Adirondacks

    Start today with breakfast at The Breakfast Club, Etc.

    The Adirondacks are pretty much synonymous with hiking, so start after breakfast head out for a walk. There’s a huge variety of hiking options listed on the Adirondack hiking website. TheCobble Hill walk is a popular one that has lovely views.

    Stop in your way (or call ahead) and reserve a spot for a Lake Placid Boat tour at the nearby Lake Placid Marins. The town of Lake Placid is on smaller Mirror Lake but the marina for larger Lake Placid is nearby and within walking distance. The boat tour takes you past some lovely and enormous vacation estates (“camps” in Adirondack vernacular), most of which have boat houses larger than most homes, and the scenery of the high peaks in their fall glory is really pretty.

    Mirror Lake Sunset

    If you still have time in the afternoon you can consider visiting some Olympic sites. The ski jumping hill is just outside of town and the Olympic stadium where the ice skating took place can be toured.

    For dinner, head to Salt of the Earth Bistro.

    Day 9 – Lake Placid to Olana to Rhinebeck

    In the morning, enjoy another very scenic drive through the mountains down to the Hudson River Valley.

    Grab lunch at the West Taghkanic Diner (3h3m drive) then continue on to tour Olana State Historic Site (16m drive), a beautiful Persian-inspired castle-like estate on the top of a hill overlooking the Hudson and Catskills. This was the home of Frederick Church, the foremost of the Hudson River School of Painters, and is a great setting and place to tour with intact interiors, furnishings, and paintings.

    From Olana it is a short drive to Rhinebeck. If you want to grab a drink, the Beekman Arms is the oldest continually operating inn in the country, and everyone from George Washington to FDR ate, drank and stayed here.

    This Hudson Valley town’s main streets are lined with independent bookstores, unique boutiques, craft beer, and delicious restaurants.

    Olana

    With extra time, consider touring Wilderstein, another one of the lovely Hudson River Mansions located right in Rhinebeck.

    Have dinner at The Amsterdam, Bia, or Cinnamon.

    Stay at theDelamater Inn, The Beekman Arms, or Mirbeau Inn and Spa.

    Day 10 – Historic Huguenot Street, Awosing Falls

    Start today by driving to New Pfalz (40m drive) and visit Historic Huguenot Street for a walking tour. This is said to be the oldest street in America with houses built in 1678 by settlers. The setting is lovely, the history is quite interesting, and the walking tours are well done.

    From here, head to nearby Minnewaska State Park (17m drive) for some lovely falls colors – especially on the pleasant stroll to Awosting Falls. The mountains here look a lot like the Catskills but are actually part of a separate mountain range. Enjoy the scenery and drive up the the nearby lake for lovely views. With time and inclination there are other lakes and falls to walk to in this delightful state park, pick up a map at the visitor center.

    Tonight have dinner at the Beekman Arms.

    Awosting Falls
    Lake In Minnewaska State Park

    Day 11 – Vanderbilt Mansion, Old Rhinebeck Aerodrome to Tarrytown

    The enormous and sumptuous Vanderbilt Mansion State Historic Site is located near Rhinebeck in nearby Hyde Park. The whole Hudson Valley is scattered with lovely mansions as the very wealthy used them to get away from crowded and hot New York City and head here. The Vanderbilt mansion is perhaps the grandest of all.

    For something different and pretty, if you have the time you can drive to Millbrook Winery. Millbrook has a lovely setting and picnic areas and the wine is quite good.

    If it’s Saturday or Sunday, head to the Old Rhinebeck airshow where you can watch planes well over 100 years old fly (and there’s plenty of melodrama in the show to go along with it). If you can’t do this, pick one of the recommended mansions near Tarrytown from tomorrow and tour it today.

    Old Rhinebeck Aerodrome

    Next drive to Tarrytown, about 1 hour away.

    Have dinner at Equus at Castle Hotel & Spa (where we also recommend you stay). Also consider Tarrytown House.

    Day 12 – Lyndhurst, Sleepy Hollow

    After breakfast at Coffee Lab Roasters in Tarrytown, head to one of the grandest of the Hudson River mansions Neogothic Lyndhurst which stands on a hill with sweeping grounds down to the Hudson. The interiors are lovely and the furnishings are original and well preserved. Reservations are required.

    Lyndhurst

    From here drive to Washington Irving’s Sunnyside where the author lived with sweeping views of the river.

    Tarrytown is also right next to Sleepy Hollow made famous by the headless horseman story written by Washington Irving. As a result Halloween is sort a big deal in this city. Be sure and stop in the old Dutch Church and adjacent cemetery and take a walk through. You can also head out to to Sleepy Hallow Lighthouse (though it isn’t as pretty as the one’s you’ve seen in Maine). Stop for lunch at Bridge View Tavern.

    After lunch head to Kykuit – the Rockefeller Estate to see an amazing art collection filled with Picasso, Henry Moore, and Alexander Calder.

    Next is a short drive to see the stunning Chagal and Matisse stained glass windows on a tour of the small Union Church of Pamlico Hills.

    Have dinner tonight back in Tarrytown at Crabtree’s Kittle House Restaurant & Inn, Goosefeather, or River Market Bar and Kitchen. If you can afford it, Blue Hill at Stone Barns is one of the best restaurants in the world.

    Day 13 – Fly Home

    Drive to Newark International Airport (or whichever one you are flying out of). Return your car and fly home.

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