NEW HAVEN & NEW CANAAN, CT
New Haven is on a pretty harbor and has some great areas and parks to walk around, but your main destination should be Yale University Art Gallery. Visiting the gallery is free. The Louis Kahn building is wonderful, as are the modern & contemporary collections. There are also many great parks closer to the Quinnipiac River and the harbor. You'll find over 400 acres of trails and picnic areas in East Rock Park and Edgerton Park has an awesome greenhouse. Grab a pizza at Frank Pepe's and then head further west for about 45 minutes to New Canaan where you'll find the Glass House. The Glass House and it's complimentary Brick House were designed by Philip Johnson between 1945 and 1948. Johnson's use of materials are in direct response to the landscape of the property. Tours are available in varying lengths. Check out the Mies van der Rohe furniture throughout the property, and stay for tours of the studio and various other buildings.
A great museum in Waterbury
A great museum in Hartford
I want to hike
COCKAPONSET STATE FOREST
Cockaponset State Forest is the second largest state forest in Connecticut so you'll find many trail and terrain options, although the hikes are dependably moderate. Chester Cedar Swamp is one of the few remaining Atlantic white cedar forests, and Pine Ledge has some good climbing options. The general vibe of the forest is hardy and rugged but there's not much elevation so the hikes are gentle. The major plus-side of checking out this forest is that there are at least eight more state parks within ten miles in the Connecticut River area, so you can cram a bunch of exploring into one day. Definitely also check out Gillette Castle State Park across the Connecticut River in East Haddam, for a tour of a monster of a home. It may be the weirdest castle you'll ever see.
Some good caves and ledges
DAY-DRINKING & PURGATORY CHASM
Worcester is home to all great diners, many amazing dive bars, and recently, some really good new things. We love Deadhorse Hill and Wormtown Brewery. But we also love grilled cheese at the Boulevard Diner, and dollar drafts at Hotel Vernon. There's way too much good stuff in Worcester, both high-brow and low-brow. And low-low-brow. There's also Ralph's Diner, Miss Worcester and Table Talk Pies. And then there's Worcester Art Museum, which is one of our favorite museums to explore all afternoon. Be sure to check out the upcoming exhibition, through February 2018- Rediscovering an American Community of Color: The Photographs of William Bullard. Then head across Park Avenue to Bancroft Tower, in Salisbury Park. This castle is weird, old, and includes a 56-foot tall tower. After the museum and castle, best in the early afternoon, head to the aforementioned Hotel Vernon in Kelley Square, where you'll sit under amazing murals while downing dollar drafts. This place is seeping with history, and it's incredibly inspiring. Ask about the murals, and ask about the speakeasy in the basement. After a couple rounds, hit up a diner or go eat a lush meal at Deadhorse Hill. About 20 minutes south of Worcester on MA-146 is a great place to go for a walk and scramble on some rocks- Purgatory Chasm, a quarter-mile split through a granite outcrop in Sutton, Massachusetts. The huge granite rocks rise as much as seventy feet from points of the lower, central trail. There is also a loop trail along the top edge of the granite that gives an amazing view of the rocks from above, and then extends into the surrounding forest. If you're in the mood to browse some neat antiques in a historic barn, don't forget to swing through the Douglas Flea Market in the Bosma Barn.
Explore old mills and walk the canal
WHALES & WINE
In New Bedford you can walk the Hurricane Barrier Harbor Walk for spectacular views of the water, and check out Fort Tabor Park and Fort Rodman. Then head to the New Bedford Whaling Museum and learn all about whales, then and now. After exploring the city, head a little west to Westport, MA. Hike around Allens Pond Wildlife Sanctuary or go for a walk on Horseneck Beach State Reservation. After all that, head to Westport Rivers Winery where you can taste out on the lawn, or tour on Saturdays. Across the street is Buzzard's Bay Brewing on a huge farm with an equally beautiful outdoor space, where you'll find award winning brews and live music.
Skee ball & the Carousel Lounge
I want a lake
Sebago Lake is Maine's second-largest, with many options for cabins to rent. Or you can camp at Sebago Lake State Park in Naples, where you'll find 1,400 acres of public land including beaches, woodlands, ponds, bogs and a river. You can rent kayaks from Sebago Trails Paddling Co. for an awesome perspective of the lake. Other Campsites to check out on the quieter, south side of the lake are Sebago Lake Family Campground or Acres of Wildlife Campground where you'll have easy access to Steep Falls Wildlife Management Area. Slightly west of the lake is Douglas Mountain. Hike the 1.8 mile Douglas Mountain Loop Trail to an old stone tower and great views of the lake.
It's the largest in Maine!
ACADIA, CAMDEN & ROCKLAND
This is a vast area to explore, but if you're this far up Route 1, you may as well try to cram it all in. Plus, Camden and Rockland are very complimentary to Bar Harbor. On your way up, you'll be hit with amazing coastal views, so try to stop for as many sights as you can. Our favorites are Pemaquid Point Lighthouse Park, many of the trails throughout the preserves of Boothbay Region Land Trust, the Whaleback Shell Midden State Historic Site, and the Marshall Point Lighthouse. When you get to Rockland, walk the 5.5 mile Rockland Harbor Trail, and check out Owls Head Lighthouse, the Maine Lighthouse Museum, and then just beyond downtown, Rockland Breakwater Lighthouse. After exploring Rockland and its many landmarks and museums, head north to Camden. Camden has a great waterfront. Seasonally, you can grab some awesome seafood at Rhumb Line. Check out Megunticook Falls right on the bay. After settling in downtown, head to the Mount Battie Trail just off of Mountain Street, and hike up 1.5 miles to Mount Battie Tower for amazing views of West Penobscot Bay. From there, you can venture further into Camden Hills State Park. Further north up Route 1, you'll find Acadia National Park which is worth the extra trek for the amazing ocean views you'll get. There's so much exploring to do here, but our favorite trails are the famous 4.1 mile Cadillac North Ridge Trail and the 3.2 mile Gorham Mountain to Ocean Path Loop.
Perfect seaside town with great food
I want to hike
PISGAH STATE PARK & MADAME SHERRI CASTLE RUINS
Pisgah State Park is the largest state park in New Hampshire, located in Cheshire County in New Hampshire. It contains seven ponds, four highland ridges, numerous wetlands, and twenty acres of old-growth forest. Hike up 1,381-foot Hubbard Hill. There are six trailheads leading into the park. There is also neighboring Hinsdale Town Forest, where you'll find many more connecting trails, including the 5.2 mile looped Mount Pisgah Trail. Then head west across Route 63 to Madame Sherri Forest. Follow the Ann Stokes Loop Trail from the Madame Sherri House ruins- the foundation, chimneys and a stone staircase are accessible from a short trail near the trailhead off Gulf Road. Read up on Madame Sherri before you go.
Busy mountain with great views
I want a lake
LAKE WINNIPESAUKEE & SOME FIRE TOWERS
Lake Winnipesaukee is the largest lake in New Hampshire and contains 258 islands. If you're visiting the lake from the south, stop first at Mount Major State Forest, or for a higher point, Belknap Mountain, both within a few miles from the lake. Mount Major's summit gives sweeping views of Lake Winnipesaukee. The Mount Major and Brook Trail Loop is a 3.8 mile hike. Hiking Belknap Mountain gives you access to a fire tower for amazing views. The Belknap Fire Tower (Red/Green Loop) Trail is a 2 mile loop. Once you've seen the lake from above, head down and explore the many harbors, bays and islands. Stay a night or a few in the many cabins for rent, or stay at a campsite. Governors and Long Island are accessible by bridge, or you can rent a kayak to explore. To round out your trip to the lake, head a little further north to Red Hill Fire Tower Loop Trail- a 3.3 mile loop near Moultonborough, New Hampshire that features a fire tower with amazing views of the lake. The trail is part of the Lakes Region Conservation Trust.
And Mount Sunapee State Park
I want to hike
BEEBE HILL STATE FOREST
Beebe Hill State Forest sits in an unassuming area on the border of New York and Massachusetts, seemingly rural without a whole lot of culture. The hill happens to sit between two special bundles of towns- to the west are Kinderhook and Chatham, and to the east are Stockbridge and Great Barrington. The New York side has really been growing in the past few years, getting doused with creative restaurant and brewery projects. Climb Beebe Hill & also check out neighboring Harvey Mountain State Forest- between the two, you'll find 30 miles of trails. The highlight is the fire tower on top of Beebe Hill. You'll get an awesome view from the tower. After a morning spent hiking and climbing the tower, head to Kinderhook Farm for their Farm Store, or on Sundays, a tour of the farm. Also very nearby is Chatham Brewing across from Crandall Theater on Main Street in Chatham. For a snack or a coffee, try the Bartlett House in nearby Ghent, an old hotel turned into a restaurant and bakery, housed in a national historic site built in the late 1800's.
The Grand Canyon of the East
The Finger Lakes of New York State are deep and long glacial carvings. Cayuga and Seneca Lakes, the largest of eleven total, are two of the deepest lakes in the United States, bottoming out below sea-level. The limestone and shale found in the area formed in the Devonian Period, and the glacial deposits that followed during the Ice Age make a rich soil for growing grapes. This area has a really interesting viticulture history, because the richness of the soil doesn't necessarily go hand-in-hand with the sometimes-bitter climate of the region. But with a little science, the Finger Lakes have become a top wine producer in this country. You can read more about the terroir of New York State here, and note it'll be more interesting if you've already had a couple glasses. Crucial to winery-hopping in the Finger Lakes Region is stopping in either Ithaca or Watkins Glen first. Beyond being great towns full of good food and interesting people, their natural landscapes are prime examples of the power of the glaciers and how they made this state. We suggest hitting Buttermilk Falls State Park after Ithaca, before heading north up the eastern side of Cayuga Lake. Then make a quick stop in Trumansburg at Taughannock Falls State Park- or if you'd like to stay awhile you can camp here too- where you'll find the highest plunging waterfall east of the Rocky Mountains. About 15 miles north of there is the first wine stop, at Thirsty Owl Wine Company, for award winning wines and spectacular views of Cayuga Lake. Just across the valley on Seneca Lake, you'll find our favorite Finger Lakes winery- Boundary Breaks Vineyard, a beautiful place really in tune with the landscape and history of the area. Their dry rieslings are wonderful. Taste their wines on the lawn, looking over the vines to the lake, all week from 11am to 5pm. Standing Stone Vineyards is another good stop with superb wine and a beautiful newly renovated tasting room. Next, take a break at Finger Lakes National Forest, a 16,212 acre forest with over 30 miles of trails to explore. The 3.8 mile Burnt Hill Loop Trail is good start, and if you want to stay longer, you can book a campsite or lean-to here, too. Finish your Finger Lake loop in Watkins Glen, at the southern tip of Seneca Lake, where you'll find amazing ledges and waterfalls, or camp a night there, and continue your tour up the western side of the lake to many more wineries.
Just follow the river
MANSIONS RESTORED & ABANDONED
Newport, Rhode Island is the best place to imagine what the Gilded Age was actually like and how the vacationers lived, but the history runs deeper than the vein of pure excess. The nineteenth century Americans who had the means to build seaside mansions in Newport also had access to international architecture and design. You'll find over-the-top extravagance, but in some of the homes simply an eclectic aesthetic and intrigue of exoticism. The Isaac Bell House shows a real cross-section of the history of Newport by showing the process of being built with privilege, run-down by the economy, re-purposed as public housing and then in its current stage, studied and viewed as a museum. A tour of the now-humble Isaac Bell house today shows the layers of rich, exotic architectural details in both full restoration and in deterioration. After visiting the Isaac Bell House, the Breakers, and another favorite, Chateau-sur-Mer, walk the Cliff Walk, a path along the coast with many good views of both the ocean and the mansions. Don't leave the area without heading west to Brenton Point State Park for an amazing, panoramic view of the ocean. Walk along the perimeter of the field and then beyond the field you'll encounter the ruins of a stable and a stone tower that will give you a view above the trees.
Cool bridges, an old windmill & great seafood
I want to camp
GEORGE WASHINGTON CAMPGROUND
George Washington Management Area in Chepachet contains 4,000 acres of trails and primitive campsites along the shores of Bowdish Lake. Stay overnight at George Washington Campground on a site surrounded by trees, cook some meals over a campfire, go for a swim in the lake, people-watch from the huge boulder on the beach, or hike the well-maintained Walkabout Loop Trails. There are various loops available to lengthen or shorten your hike. You can also hop on the RI North-South Trail to add miles to your hike. You'll find a crossing of that trail as you're hiking along Wilbur Pond. It's a quiet, simple forest and campground with a lot of privacy and lots of space to explore. There are also two Adirondack style Shelters available by reservation. Bring some good campfire food, get the campfire roaring, and have a blast.
And Watchaug Pond in Charlestown
A SCENIC CITY
Burlington, Vermont has a different aesthetic than the rest of New England. The highlight is Lake Champlain and Burlington Bay, and the way the entire city slopes towards the water. But before you get to the city, hit Audubon Vermont: Green Mountain Audubon Center, just under 20 miles south-east, and also the nearby Birds of Vermont, a museum containing more than 500 wood carved birds. Along the Winooski River you'll find a nice walk along the Champlain Mill Path on the Winooski side. On the Burlington side of the river is The Salmon Hole. Along Lake Champlain you can follow the Island Line Rail Trail for 14 miles. The best part of this rail trail is when, north of Burlington, it turns into a breakwater in the lake, leading to Grand Isle from Causeway Park. Then heading south, past the South End on Flynn Avenue, check out the World's Tallest Filing Cabinet- literally a heaping stack of old filing cabinets on the side of the road. Foam Brewers near Waterfront Park has great beer and snacks, plus live music and a generally good vibe. Zero Gravity Brewery is also a good stop for beer and flatbread pizza, and you can tell they care about the relationship between bread baking and beer making. For a special meal try Misery Loves Company across the river in Winooski, or on your way out of the city try Hen of the Wood.
I want to hike
A QUEST FOR FIRE TOWERS
Finding all of these fire towers can turn into quite the trek, but they all fall along a beautiful route up to northern Vermont, so if you have the means, try it. Starting in the Green Mountains, hike up Stratton Mountain. You can start at the base and take The Long Trail to Stratton Mountain up, which is a 6.7 mile total out-and-back hike, or you can conserve time and energy and take Stratton Mountain's gondola up all summer and into peak leaf-peeping season. Next is Okemo Mountain, via the Healdville Trail, a 5.8 mile out-and-back hike where you'll again get amazing tower views of the Vermont Landscape. Okemo is another ski resort town that's still bustling with hikers all summer, which sits about an hour north of Stratton on the scenic VT Route 100, one of the prettiest drives in the country. From Okemo, head a little east to Mount Ascutney. Take the 5.2 mile out-and-back Weathersfield Trail to the summit, where you can climb a fire tower. Hitting all of these towers isn't a day trip, but there are great places to stay in Vermont- farms, cabins, and camping included. If primitive camping is your thing, stay a night in Coolidge State Park, or if you want a few more accommodations, check out Forest Echo Farm Cabins for some secluded and rustic cabins. If you really want to trek up to way-northern Vermont, you can find three more good fire towers- Spruce Mountain near Plainfield, Mount Elmore near Wolcott, and lastly, Bald Mountain, way up north near Orleans. Good luck!