Vanessa's Guidebook
Sports
Places to play
Go Sox! If the Boys of Summer are in town, you’ve got to go to a game! If your budget is tight, grab bleacher seats—they’re only 40 bucks! Wear a hat and load up on sunscreen.
815 locals recommend
Fenway Park
4 Jersey StGo Sox! If the Boys of Summer are in town, you’ve got to go to a game! If your budget is tight, grab bleacher seats—they’re only 40 bucks! Wear a hat and load up on sunscreen.
Head north to the Contoocook River Canoe Company for a day of River adventure. They’ll drive your group with your kayaks upriver 9 miles and you can paddle your way back. Be sure to pack a big lunch—you’ll want to stop half way at Daily Island to picnic. It’s a scene out of the movies!
Contoocook River
Head north to the Contoocook River Canoe Company for a day of River adventure. They’ll drive your group with your kayaks upriver 9 miles and you can paddle your way back. Be sure to pack a big lunch—you’ll want to stop half way at Daily Island to picnic. It’s a scene out of the movies!
If you like to play tennis, check out Packer Ellis, just three blocks (or a kayak ride) from the house. There are a dozen clay courts. The cost is about $16 per person to play—morning and evening hours. Grab a day pass at winrec.com. Forgot your tennis racquet? Check the sports locker downstairs. We have plenty!
Packer-Ellis Courts
Palmer StreetIf you like to play tennis, check out Packer Ellis, just three blocks (or a kayak ride) from the house. There are a dozen clay courts. The cost is about $16 per person to play—morning and evening hours. Grab a day pass at winrec.com. Forgot your tennis racquet? Check the sports locker downstairs. We have plenty!
Nature
Hiking, camping, swimming—all things outdoors
By far our favorite beach! Low tide is ⭐️⭐️⭐️⭐️⭐️ for kids. Quintessential New England! Want some more adventure?Grab a tent and a couple of sleeping bags from the sports locker and make a reservation at Cape Ann Campground. It’s a mile from Wingaersheek and a super easy overnight!
66 locals recommend
Wingaersheek Beach
By far our favorite beach! Low tide is ⭐️⭐️⭐️⭐️⭐️ for kids. Quintessential New England! Want some more adventure?Grab a tent and a couple of sleeping bags from the sports locker and make a reservation at Cape Ann Campground. It’s a mile from Wingaersheek and a super easy overnight!
Right here in Winchester, you can hike miles of beautiful woodland trails at the Middlesex Fells. Pick up a path at any of many trailheads in Winchester—Hillcrest Parkway and the Long Pond parking lot on South Border Road are our favorite spots to enter.
74 locals recommend
Middlesex Fells Reservation
4 Woodland RdRight here in Winchester, you can hike miles of beautiful woodland trails at the Middlesex Fells. Pick up a path at any of many trailheads in Winchester—Hillcrest Parkway and the Long Pond parking lot on South Border Road are our favorite spots to enter.
This very easy hike is two hours north, but it’s so fun. Locally known as “The Goshen Ocean,” Lake Gunnison is a man made reservoir surrounded by an easy hiking trail. The best part is a rope swing that is perfect for kids ages five and up. Our family could spend all day here. The water is shallow and warm. They can pick up the rope on the ground or super high in a tree. It’s awesome. Drive back south through Sunapee. Stop at Sanctuary Farm for the best ice cream ever, made by a teenager who’s been making ice cream at his parents’ dairy farm since he was 9 years old. There’s a big field to play in, volleyball nets, and goats and donkeys to pat and feed. True summer magic. To extend the adventure, drive along beautiful Lake Sunapee and visit Sunapee Harbor, home to Steve Tyler. You can grab a bite at The Anchorage Restaurant (where Joe Perry worked as a teenager). We call ice cream before dinner and upside down dinner, which makes it okay. 🙃
Lake Gunnison
This very easy hike is two hours north, but it’s so fun. Locally known as “The Goshen Ocean,” Lake Gunnison is a man made reservoir surrounded by an easy hiking trail. The best part is a rope swing that is perfect for kids ages five and up. Our family could spend all day here. The water is shallow and warm. They can pick up the rope on the ground or super high in a tree. It’s awesome. Drive back south through Sunapee. Stop at Sanctuary Farm for the best ice cream ever, made by a teenager who’s been making ice cream at his parents’ dairy farm since he was 9 years old. There’s a big field to play in, volleyball nets, and goats and donkeys to pat and feed. True summer magic. To extend the adventure, drive along beautiful Lake Sunapee and visit Sunapee Harbor, home to Steve Tyler. You can grab a bite at The Anchorage Restaurant (where Joe Perry worked as a teenager). We call ice cream before dinner and upside down dinner, which makes it okay. 🙃
Amusement
Amusement parks
The best amusement park ever. It’s a quick trip up 93. Well cared for rides, clean and tidy, decent junk food, water park, reasonably priced… I honestly think it’s better than Disney. 😉
60 locals recommend
Canobie Lake Park
85 N Policy StThe best amusement park ever. It’s a quick trip up 93. Well cared for rides, clean and tidy, decent junk food, water park, reasonably priced… I honestly think it’s better than Disney. 😉
I don’t care how old you are, you will be whooping down this mountain coaster! It’s so much fun!! There’s also a ropes course and a mountain bike trail that starts at the summit. You can make a great day of adventure along route 2 in western Massachusetts. The Mohawk Trail is beautiful and scenic! Don’t stop there though. Make a reservation with Zoar Outoor or Crab Apple for white water rafting on the Deerfield. While you’re there, you may as well hit Mass MOCA. you may even be able to catch a concert! It’s a long drive and totally worth it!
Thunderbolt Mountain Coaster
66D Thunder Mountain RoadI don’t care how old you are, you will be whooping down this mountain coaster! It’s so much fun!! There’s also a ropes course and a mountain bike trail that starts at the summit. You can make a great day of adventure along route 2 in western Massachusetts. The Mohawk Trail is beautiful and scenic! Don’t stop there though. Make a reservation with Zoar Outoor or Crab Apple for white water rafting on the Deerfield. While you’re there, you may as well hit Mass MOCA. you may even be able to catch a concert! It’s a long drive and totally worth it!
Sightseeing
It’s a must-visit for tourists. Walk the freedom trail, take a tour, do some shopping, eat an ice cream cone, ride the merry go round on Rose Kennedy Greenway, pick up a cannoli in the North End.
517 locals recommend
Faneuil Hall Marketplace
1 S Market StIt’s a must-visit for tourists. Walk the freedom trail, take a tour, do some shopping, eat an ice cream cone, ride the merry go round on Rose Kennedy Greenway, pick up a cannoli in the North End.
If you’ve never been, you must make a day for Provincetown. Easiest way to get there is a ferry from Boston. Catch the earliest boat you can because you’ll want to whole day! Rent a bike when you get there and pedal to Racepoint Beach. The wooded bike paths are AMAZING!! White sand, stunning dunes, and seals will greet you at the tip of the curl. Head back and enjoy the terrific restaurants and shopping along Commecial Street. Make sure to pick up fudge! Yummm!!!
328 locals recommend
Provincetown
If you’ve never been, you must make a day for Provincetown. Easiest way to get there is a ferry from Boston. Catch the earliest boat you can because you’ll want to whole day! Rent a bike when you get there and pedal to Racepoint Beach. The wooded bike paths are AMAZING!! White sand, stunning dunes, and seals will greet you at the tip of the curl. Head back and enjoy the terrific restaurants and shopping along Commecial Street. Make sure to pick up fudge! Yummm!!!
A little fishing village filled with art, scenic views, and delicious seafood. You like oysters? This is your place.
83 locals recommend
Rockport
A little fishing village filled with art, scenic views, and delicious seafood. You like oysters? This is your place.
All sorts of fun things happen on Boston Common, but our favorite is Shakespeare on the Common. Check online to see if they’re performing during your visit. Pack a cooler and a lawn chair (in the shed under the screen porch) and head in for the evening. It is soooo fun. Get there early for best seats. You may need to reserve online due to pandemic.
84 locals recommend
Boston Common Visitors Center
139 Tremont StAll sorts of fun things happen on Boston Common, but our favorite is Shakespeare on the Common. Check online to see if they’re performing during your visit. Pack a cooler and a lawn chair (in the shed under the screen porch) and head in for the evening. It is soooo fun. Get there early for best seats. You may need to reserve online due to pandemic.
Food scene
Okay, so it’s pub food. Not the best you’ll ever have, but the atmosphere is really great and they frequently have a one man band playing country and folk music. Lots of outdoor seating, pretty flower boxes, and it’s a two minute walk from home.
Black Horse Tavern
32 Waterfield RdOkay, so it’s pub food. Not the best you’ll ever have, but the atmosphere is really great and they frequently have a one man band playing country and folk music. Lots of outdoor seating, pretty flower boxes, and it’s a two minute walk from home.
Historic and very Bostonian, Charlestown's Warren Tavern is a famous local pub. It's going to be crowded so get there early or be prepared to wait for a table. Parking can be tricky but it's worth the effort to eat where our founding fathers ate!
52 locals recommend
The Warren Tavern
2 Pleasant StHistoric and very Bostonian, Charlestown's Warren Tavern is a famous local pub. It's going to be crowded so get there early or be prepared to wait for a table. Parking can be tricky but it's worth the effort to eat where our founding fathers ate!
Bow Market is a cool collection of pop up shops anchored by a brewery. There is a comedy stage there, jewelry makers, plant shops, resalers. It’s a local delight in Somerville. My teenage girls and I will often grab açaí bowls at Nu Kitcen on Washington Street in Somerville then walk to Bow for vintage clothes and record shopping. It’s very hipster and you feel a little cooler hanging out there.
31 locals recommend
Bow Market
1 Bow Mkt WyBow Market is a cool collection of pop up shops anchored by a brewery. There is a comedy stage there, jewelry makers, plant shops, resalers. It’s a local delight in Somerville. My teenage girls and I will often grab açaí bowls at Nu Kitcen on Washington Street in Somerville then walk to Bow for vintage clothes and record shopping. It’s very hipster and you feel a little cooler hanging out there.
This is my favorite restaurant. Mexican. Authentic. Magical. It’s tucked into an alley between Newbury Street and Comm Ave. If you didn’t know it was there, you wouldn’t know it was there. Spend an afternoon shopping on Newbury, starting at the Public Garden. Make your way down to Gloucester and hook a right, then turn left down the alleyway. On the left, you’ll see a red wooden tucked into a brick wall. That’s Casa Romero. I hope you love it!
17 locals recommend
Casa Romero
30 Gloucester StThis is my favorite restaurant. Mexican. Authentic. Magical. It’s tucked into an alley between Newbury Street and Comm Ave. If you didn’t know it was there, you wouldn’t know it was there. Spend an afternoon shopping on Newbury, starting at the Public Garden. Make your way down to Gloucester and hook a right, then turn left down the alleyway. On the left, you’ll see a red wooden tucked into a brick wall. That’s Casa Romero. I hope you love it!
Lucia’s is the local spot for Italian. It’s a solid B+. The bar is fun but does get crowded. Make a reservation if you’d like to sit outside.
Lucia Ristorante / Winchester
13 Mt Vernon StLucia’s is the local spot for Italian. It’s a solid B+. The bar is fun but does get crowded. Make a reservation if you’d like to sit outside.
I recommend A Tavola because it’s cute and cozy and super close—just two short blocks away. The atmosphere is wonderful. The food is super fresh. Appetizers are generally yummy. Main courses are hit or miss and IMHO overpriced. Desserts have been awesome. Be sure to make a rezzie. There is a decent amount of outdoor seating.
A Tavola
34 Church StreetI recommend A Tavola because it’s cute and cozy and super close—just two short blocks away. The atmosphere is wonderful. The food is super fresh. Appetizers are generally yummy. Main courses are hit or miss and IMHO overpriced. Desserts have been awesome. Be sure to make a rezzie. There is a decent amount of outdoor seating.
Music
If you like Indie music, check out the playlist at Once. It’s super local and some truly awesome bands come through!
ONCE Ballroom
0 Windsor PlaceIf you like Indie music, check out the playlist at Once. It’s super local and some truly awesome bands come through!
The coolest bands come here. Check out what’s happening at HOB and get your tickets in advance. Fenway Park may also have some incredible shows this summer. My daughter and I caught Green Day there last summer and it was literally the best show I’ve ever seen—and I’ve seen a lot!!
77 locals recommend
House of Blues Boston
15 Lansdowne StThe coolest bands come here. Check out what’s happening at HOB and get your tickets in advance. Fenway Park may also have some incredible shows this summer. My daughter and I caught Green Day there last summer and it was literally the best show I’ve ever seen—and I’ve seen a lot!!
City/town information
Stockbridge and its neighbor Great Barrington are two beautiful cities to visit while visiting Massachusetts. Enjoy a full day of history, shopping, restaurants, nature, and music. Catch a show on the lawn at Tanglewood or indulge with a day pass at famous yogi retreat center Kripalu in Lenox.
69 locals recommend
Stockbridge
Stockbridge and its neighbor Great Barrington are two beautiful cities to visit while visiting Massachusetts. Enjoy a full day of history, shopping, restaurants, nature, and music. Catch a show on the lawn at Tanglewood or indulge with a day pass at famous yogi retreat center Kripalu in Lenox.